diff --git a/Cargo.lock b/Cargo.lock
index c2c06a2adb1..b2ae22b6abd 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -101,6 +101,12 @@ version = "0.4.7"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "4d25d88fd6b8041580a654f9d0c581a047baee2b3efee13275f2fc392fc75034"
 
+[[package]]
+name = "array_tool"
+version = "1.0.3"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "8f8cb5d814eb646a863c4f24978cff2880c4be96ad8cde2c0f0678732902e271"
+
 [[package]]
 name = "arrayref"
 version = "0.3.6"
@@ -1630,6 +1636,32 @@ version = "0.11.15"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "92c245af8786f6ac35f95ca14feca9119e71339aaab41e878e7cdd655c97e9e5"
 
+[[package]]
+name = "jsondocck"
+version = "0.1.0"
+dependencies = [
+ "getopts",
+ "jsonpath_lib",
+ "lazy_static",
+ "regex",
+ "serde",
+ "serde_json",
+ "shlex",
+]
+
+[[package]]
+name = "jsonpath_lib"
+version = "0.2.6"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "61352ec23883402b7d30b3313c16cbabefb8907361c4eb669d990cbb87ceee5a"
+dependencies = [
+ "array_tool",
+ "env_logger 0.7.1",
+ "log",
+ "serde",
+ "serde_json",
+]
+
 [[package]]
 name = "jsonrpc-client-transports"
 version = "14.2.1"
@@ -2854,9 +2886,9 @@ dependencies = [
 
 [[package]]
 name = "regex"
-version = "1.3.9"
+version = "1.4.3"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "9c3780fcf44b193bc4d09f36d2a3c87b251da4a046c87795a0d35f4f927ad8e6"
+checksum = "d9251239e129e16308e70d853559389de218ac275b515068abc96829d05b948a"
 dependencies = [
  "aho-corasick",
  "memchr",
@@ -2876,9 +2908,9 @@ dependencies = [
 
 [[package]]
 name = "regex-syntax"
-version = "0.6.18"
+version = "0.6.22"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "26412eb97c6b088a6997e05f69403a802a92d520de2f8e63c2b65f9e0f47c4e8"
+checksum = "b5eb417147ba9860a96cfe72a0b93bf88fee1744b5636ec99ab20c1aa9376581"
 
 [[package]]
 name = "remote-test-client"
@@ -4578,6 +4610,7 @@ version = "1.0.59"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "dcac07dbffa1c65e7f816ab9eba78eb142c6d44410f4eeba1e26e4f5dfa56b95"
 dependencies = [
+ "indexmap",
  "itoa",
  "ryu",
  "serde",
diff --git a/Cargo.toml b/Cargo.toml
index 204c92045b1..5bd1147cad5 100644
--- a/Cargo.toml
+++ b/Cargo.toml
@@ -31,6 +31,7 @@ members = [
   "src/tools/rustdoc-themes",
   "src/tools/unicode-table-generator",
   "src/tools/expand-yaml-anchors",
+  "src/tools/jsondocck",
 ]
 
 exclude = [
diff --git a/src/bootstrap/test.rs b/src/bootstrap/test.rs
index 2e8c574044e..335a1731002 100644
--- a/src/bootstrap/test.rs
+++ b/src/bootstrap/test.rs
@@ -1011,6 +1011,13 @@ note: if you're sure you want to do this, please open an issue as to why. In the
             cmd.arg("--rustdoc-path").arg(builder.rustdoc(compiler));
         }
 
+        if mode == "rustdoc-json" {
+            // Use the beta compiler for jsondocck
+            let json_compiler = compiler.with_stage(0);
+            cmd.arg("--jsondocck-path")
+                .arg(builder.ensure(tool::JsonDocCk { compiler: json_compiler, target }));
+        }
+
         if mode == "run-make" && suite.ends_with("fulldeps") {
             cmd.arg("--rust-demangler-path").arg(builder.tool_exe(Tool::RustDemangler));
         }
diff --git a/src/bootstrap/tool.rs b/src/bootstrap/tool.rs
index dc786249d99..835b8beb0e7 100644
--- a/src/bootstrap/tool.rs
+++ b/src/bootstrap/tool.rs
@@ -367,6 +367,7 @@ bootstrap_tool!(
     RustdocTheme, "src/tools/rustdoc-themes", "rustdoc-themes";
     ExpandYamlAnchors, "src/tools/expand-yaml-anchors", "expand-yaml-anchors";
     LintDocs, "src/tools/lint-docs", "lint-docs";
+    JsonDocCk, "src/tools/jsondocck", "jsondocck";
 );
 
 #[derive(Debug, Copy, Clone, Hash, PartialEq, Eq, Ord, PartialOrd)]
diff --git a/src/test/rustdoc-json/check_missing_items.py b/src/etc/check_missing_items.py
similarity index 99%
rename from src/test/rustdoc-json/check_missing_items.py
rename to src/etc/check_missing_items.py
index 3a3bf7fa3ed..c7ca0134f9c 100644
--- a/src/test/rustdoc-json/check_missing_items.py
+++ b/src/etc/check_missing_items.py
@@ -4,6 +4,8 @@
 # `index` or `paths`. It DOES NOT check that the structure of the produced json is actually in
 # any way correct, for example an empty map would pass.
 
+# FIXME: Better error output
+
 import sys
 import json
 
diff --git a/src/test/rustdoc-json/compare.py b/src/test/rustdoc-json/compare.py
deleted file mode 100644
index 6a921266336..00000000000
--- a/src/test/rustdoc-json/compare.py
+++ /dev/null
@@ -1,132 +0,0 @@
-#!/usr/bin/env python
-
-# This script can check that an expected json blob is a subset of what actually gets produced.
-# The comparison is independent of the value of IDs (which are unstable) and instead uses their
-# relative ordering to check them against eachother by looking them up in their respective blob's
-# `index` or `paths` mappings. To add a new test run `rustdoc --output-format json -o . yourtest.rs`
-# and then create `yourtest.expected` by stripping unnecessary details from `yourtest.json`. If
-# you're on windows, replace `\` with `/`.
-
-# WARNING: The error messages produced by this may be misleading, in the case of list re-ordering
-#          it may point to apparently unrelated keys.
-
-import copy
-import sys
-import json
-import types
-
-# Used instead of the string ids when used as references.
-# Not used as keys in `index` or `paths`
-class ID(str):
-    pass
-
-
-class SubsetException(Exception):
-    def __init__(self, msg, trace):
-        self.msg = msg
-        self.trace = msg
-        super().__init__("{}: {}".format(trace, msg))
-
-
-def check_subset(expected_main, actual_main, base_dir):
-    expected_index = expected_main["index"]
-    expected_paths = expected_main["paths"]
-    actual_index = actual_main["index"]
-    actual_paths = actual_main["paths"]
-    already_checked = set()
-
-    def _check_subset(expected, actual, trace):
-        expected_type = type(expected)
-        actual_type = type(actual)
-
-        if actual_type is str:
-            actual = normalize(actual).replace(base_dir, "$TEST_BASE_DIR")
-
-        if expected_type is not actual_type:
-            raise SubsetException(
-                "expected type `{}`, got `{}`".format(expected_type, actual_type), trace
-            )
-
-
-        if expected_type in (int, bool, str) and expected != actual:
-            raise SubsetException("expected `{}`, got: `{}`".format(expected, actual), trace)
-        if expected_type is dict:
-            for key in expected:
-                if key not in actual:
-                    raise SubsetException(
-                        "Key `{}` not found in output".format(key), trace
-                    )
-                new_trace = copy.deepcopy(trace)
-                new_trace.append(key)
-                _check_subset(expected[key], actual[key], new_trace)
-        elif expected_type is list:
-            expected_elements = len(expected)
-            actual_elements = len(actual)
-            if expected_elements != actual_elements:
-                raise SubsetException(
-                    "Found {} items, expected {}".format(
-                        expected_elements, actual_elements
-                    ),
-                    trace,
-                )
-            for expected, actual in zip(expected, actual):
-                new_trace = copy.deepcopy(trace)
-                new_trace.append(expected)
-                _check_subset(expected, actual, new_trace)
-        elif expected_type is ID and expected not in already_checked:
-            already_checked.add(expected)
-            _check_subset(
-                expected_index.get(expected, {}), actual_index.get(actual, {}), trace
-            )
-            _check_subset(
-                expected_paths.get(expected, {}), actual_paths.get(actual, {}), trace
-            )
-
-    _check_subset(expected_main["root"], actual_main["root"], [])
-
-
-def rustdoc_object_hook(obj):
-    # No need to convert paths, index and external_crates keys to ids, since
-    # they are the target of resolution, and never a source itself.
-    if "id" in obj and obj["id"]:
-        obj["id"] = ID(obj["id"])
-    if "root" in obj:
-        obj["root"] = ID(obj["root"])
-    if "items" in obj:
-        obj["items"] = [ID(id) for id in obj["items"]]
-    if "variants" in obj:
-        obj["variants"] = [ID(id) for id in obj["variants"]]
-    if "fields" in obj:
-        obj["fields"] = [ID(id) for id in obj["fields"]]
-    if "impls" in obj:
-        obj["impls"] = [ID(id) for id in obj["impls"]]
-    if "implementors" in obj:
-        obj["implementors"] = [ID(id) for id in obj["implementors"]]
-    if "links" in obj:
-        obj["links"] = {s: ID(id) for s, id in obj["links"]}
-    if "variant_kind" in obj and obj["variant_kind"] == "struct":
-        obj["variant_inner"] = [ID(id) for id in obj["variant_inner"]]
-    return obj
-
-
-def main(expected_fpath, actual_fpath, base_dir):
-    print(
-        "checking that {} is a logical subset of {}".format(
-            expected_fpath, actual_fpath
-        )
-    )
-    with open(expected_fpath) as expected_file:
-        expected_main = json.load(expected_file, object_hook=rustdoc_object_hook)
-    with open(actual_fpath) as actual_file:
-        actual_main = json.load(actual_file, object_hook=rustdoc_object_hook)
-    check_subset(expected_main, actual_main, base_dir)
-    print("all checks passed")
-
-def normalize(s):
-    return s.replace('\\', '/')
-
-if __name__ == "__main__":
-    if len(sys.argv) < 4:
-        print("Usage: `compare.py expected.json actual.json test-dir`")
-    else:
-        main(sys.argv[1], sys.argv[2], normalize(sys.argv[3]))
diff --git a/src/test/rustdoc-json/nested.expected b/src/test/rustdoc-json/nested.expected
deleted file mode 100644
index 80070e75f1e..00000000000
--- a/src/test/rustdoc-json/nested.expected
+++ /dev/null
@@ -1,196 +0,0 @@
-{
-  "crate_version": null,
-  "external_crates": {},
-  "format_version": 1,
-  "includes_private": false,
-  "index": {
-    "0:0": {
-      "attrs": [],
-      "crate_id": 0,
-      "deprecation": null,
-      "docs": "",
-      "id": "0:0",
-      "inner": {
-        "is_crate": true,
-        "items": [
-          "0:3"
-        ]
-      },
-      "kind": "module",
-      "links": {},
-      "name": "nested",
-      "source": {
-        "begin": [
-          2,
-          0
-        ],
-        "end": [
-          7,
-          1
-        ],
-        "filename": "$TEST_BASE_DIR/nested.rs"
-      },
-      "visibility": "public"
-    },
-    "0:3": {
-      "attrs": [],
-      "crate_id": 0,
-      "deprecation": null,
-      "docs": "",
-      "id": "0:3",
-      "inner": {
-        "is_crate": false,
-        "items": [
-          "0:4",
-          "0:7"
-        ]
-      },
-      "kind": "module",
-      "links": {},
-      "name": "l1",
-      "source": {
-        "begin": [
-          2,
-          0
-        ],
-        "end": [
-          7,
-          1
-        ],
-        "filename": "$TEST_BASE_DIR/nested.rs"
-      },
-      "visibility": "public"
-    },
-    "0:4": {
-      "attrs": [],
-      "crate_id": 0,
-      "deprecation": null,
-      "docs": "",
-      "id": "0:4",
-      "inner": {
-        "is_crate": false,
-        "items": [
-          "0:5"
-        ]
-      },
-      "kind": "module",
-      "links": {},
-      "name": "l3",
-      "source": {
-        "begin": [
-          3,
-          4
-        ],
-        "end": [
-          5,
-          5
-        ],
-        "filename": "$TEST_BASE_DIR/nested.rs"
-      },
-      "visibility": "public"
-    },
-    "0:5": {
-      "attrs": [],
-      "crate_id": 0,
-      "deprecation": null,
-      "docs": "",
-      "id": "0:5",
-      "inner": {
-        "fields": [],
-        "fields_stripped": false,
-        "generics": {
-          "params": [],
-          "where_predicates": []
-        },
-        "impls": [
-          "0:10",
-          "0:11",
-          "0:12",
-          "0:14",
-          "0:15"
-        ],
-        "struct_type": "unit"
-      },
-      "kind": "struct",
-      "links": {},
-      "name": "L4",
-      "source": {
-        "begin": [
-          4,
-          8
-        ],
-        "end": [
-          4,
-          22
-        ],
-        "filename": "$TEST_BASE_DIR/nested.rs"
-      },
-      "visibility": "public"
-    },
-    "0:7": {
-      "attrs": [],
-      "crate_id": 0,
-      "deprecation": null,
-      "docs": "",
-      "id": "0:7",
-      "inner": {
-        "glob": false,
-        "id": "0:5",
-        "name": "L4",
-        "span": "l3::L4"
-      },
-      "kind": "import",
-      "links": {},
-      "name": null,
-      "source": {
-        "begin": [
-          6,
-          4
-        ],
-        "end": [
-          6,
-          19
-        ],
-        "filename": "$TEST_BASE_DIR/nested.rs"
-      },
-      "visibility": "public"
-    }
-  },
-  "paths": {
-    "0:0": {
-      "crate_id": 0,
-      "kind": "module",
-      "path": [
-        "nested"
-      ]
-    },
-    "0:3": {
-      "crate_id": 0,
-      "kind": "module",
-      "path": [
-        "nested",
-        "l1"
-      ]
-    },
-    "0:4": {
-      "crate_id": 0,
-      "kind": "module",
-      "path": [
-        "nested",
-        "l1",
-        "l3"
-      ]
-    },
-    "0:5": {
-      "crate_id": 0,
-      "kind": "struct",
-      "path": [
-        "nested",
-        "l1",
-        "l3",
-        "L4"
-      ]
-    }
-  },
-  "root": "0:0"
-}
\ No newline at end of file
diff --git a/src/test/rustdoc-json/nested.rs b/src/test/rustdoc-json/nested.rs
index e460b343d37..7e705255d98 100644
--- a/src/test/rustdoc-json/nested.rs
+++ b/src/test/rustdoc-json/nested.rs
@@ -1,7 +1,24 @@
 // edition:2018
+
+// @has nested.json "$.index[*][?(@.name=='nested')].kind" \"module\"
+// @has - "$.index[*][?(@.name=='nested')].inner.is_crate" true
+// @count - "$.index[*][?(@.name=='nested')].inner.items[*]" 1
+
+// @has nested.json "$.index[*][?(@.name=='l1')].kind" \"module\"
+// @has - "$.index[*][?(@.name=='l1')].inner.is_crate" false
+// @count - "$.index[*][?(@.name=='l1')].inner.items[*]" 2
 pub mod l1 {
+
+    // @has nested.json "$.index[*][?(@.name=='l3')].kind" \"module\"
+    // @has - "$.index[*][?(@.name=='l3')].inner.is_crate" false
+    // @count - "$.index[*][?(@.name=='l3')].inner.items[*]" 1
     pub mod l3 {
+
+        // @has nested.json "$.index[*][?(@.name=='L4')].kind" \"struct\"
+        // @has - "$.index[*][?(@.name=='L4')].inner.struct_type" \"unit\"
         pub struct L4;
     }
+    // @has nested.json "$.index[*][?(@.inner.span=='l3::L4')].kind" \"import\"
+    // @has - "$.index[*][?(@.inner.span=='l3::L4')].inner.glob" false
     pub use l3::L4;
 }
diff --git a/src/test/rustdoc-json/structs.expected b/src/test/rustdoc-json/structs.expected
deleted file mode 100644
index 799829de3fd..00000000000
--- a/src/test/rustdoc-json/structs.expected
+++ /dev/null
@@ -1,456 +0,0 @@
-{
-  "root": "0:0",
-  "version": null,
-  "includes_private": false,
-  "index": {
-    "0:9": {
-      "crate_id": 0,
-      "name": "Unit",
-      "source": {
-        "filename": "$TEST_BASE_DIR/structs.rs",
-        "begin": [
-          7,
-          0
-        ],
-        "end": [
-          7,
-          16
-        ]
-      },
-      "visibility": "public",
-      "docs": "",
-      "links": {},
-      "attrs": [],
-      "deprecation": null,
-      "kind": "struct",
-      "inner": {
-        "struct_type": "unit",
-        "generics": {
-          "params": [],
-          "where_predicates": []
-        },
-        "fields_stripped": false,
-        "fields": []
-      }
-    },
-    "0:8": {
-      "crate_id": 0,
-      "name": "1",
-      "source": {
-        "filename": "$TEST_BASE_DIR/structs.rs",
-        "begin": [
-          5,
-          22
-        ],
-        "end": [
-          5,
-          28
-        ]
-      },
-      "visibility": "default",
-      "docs": "",
-      "links": {},
-      "attrs": [],
-      "deprecation": null,
-      "kind": "struct_field",
-      "inner": {
-        "kind": "resolved_path",
-        "inner": {
-          "name": "String",
-          "id": "5:5035",
-          "args": {
-            "angle_bracketed": {
-              "args": [],
-              "bindings": []
-            }
-          },
-          "param_names": []
-        }
-      }
-    },
-    "0:18": {
-      "crate_id": 0,
-      "name": "stuff",
-      "source": {
-        "filename": "$TEST_BASE_DIR/structs.rs",
-        "begin": [
-          15,
-          4
-        ],
-        "end": [
-          15,
-          17
-        ]
-      },
-      "visibility": "default",
-      "docs": "",
-      "links": {},
-      "attrs": [],
-      "deprecation": null,
-      "kind": "struct_field",
-      "inner": {
-        "kind": "resolved_path",
-        "inner": {
-          "name": "Vec",
-          "id": "5:4322",
-          "args": {
-            "angle_bracketed": {
-              "args": [
-                {
-                  "type": {
-                    "kind": "generic",
-                    "inner": "T"
-                  }
-                }
-              ],
-              "bindings": []
-            }
-          },
-          "param_names": []
-        }
-      }
-    },
-    "0:11": {
-      "crate_id": 0,
-      "name": "WithPrimitives",
-      "source": {
-        "filename": "$TEST_BASE_DIR/structs.rs",
-        "begin": [
-          9,
-          0
-        ],
-        "end": [
-          12,
-          1
-        ]
-      },
-      "visibility": "public",
-      "docs": "",
-      "links": {},
-      "attrs": [],
-      "deprecation": null,
-      "kind": "struct",
-      "inner": {
-        "struct_type": "plain",
-        "generics": {
-          "params": [
-            {
-              "name": "'a",
-              "kind": "lifetime"
-            }
-          ],
-          "where_predicates": []
-        },
-        "fields_stripped": true
-      }
-    },
-    "0:14": {
-      "crate_id": 0,
-      "name": "s",
-      "source": {
-        "filename": "$TEST_BASE_DIR/structs.rs",
-        "begin": [
-          11,
-          4
-        ],
-        "end": [
-          11,
-          14
-        ]
-      },
-      "visibility": "default",
-      "docs": "",
-      "links": {},
-      "attrs": [],
-      "deprecation": null,
-      "kind": "struct_field",
-      "inner": {
-        "kind": "borrowed_ref",
-        "inner": {
-          "lifetime": "'a",
-          "mutable": false,
-          "type": {
-            "kind": "primitive",
-            "inner": "str"
-          }
-        }
-      }
-    },
-    "0:19": {
-      "crate_id": 0,
-      "name": "things",
-      "source": {
-        "filename": "$TEST_BASE_DIR/structs.rs",
-        "begin": [
-          16,
-          4
-        ],
-        "end": [
-          16,
-          25
-        ]
-      },
-      "visibility": "default",
-      "docs": "",
-      "links": {},
-      "attrs": [],
-      "deprecation": null,
-      "kind": "struct_field",
-      "inner": {
-        "kind": "resolved_path",
-        "inner": {
-          "name": "HashMap",
-          "id": "1:6600",
-          "args": {
-            "angle_bracketed": {
-              "args": [
-                {
-                  "type": {
-                    "kind": "generic",
-                    "inner": "U"
-                  }
-                },
-                {
-                  "type": {
-                    "kind": "generic",
-                    "inner": "U"
-                  }
-                }
-              ],
-              "bindings": []
-            }
-          },
-          "param_names": []
-        }
-      }
-    },
-    "0:15": {
-      "crate_id": 0,
-      "name": "WithGenerics",
-      "source": {
-        "filename": "$TEST_BASE_DIR/structs.rs",
-        "begin": [
-          14,
-          0
-        ],
-        "end": [
-          17,
-          1
-        ]
-      },
-      "visibility": "public",
-      "docs": "",
-      "links": {},
-      "attrs": [],
-      "deprecation": null,
-      "kind": "struct",
-      "inner": {
-        "struct_type": "plain",
-        "generics": {
-          "params": [
-            {
-              "name": "T",
-              "kind": {
-                "type": {
-                  "bounds": [],
-                  "default": null
-                }
-              }
-            },
-            {
-              "name": "U",
-              "kind": {
-                "type": {
-                  "bounds": [],
-                  "default": null
-                }
-              }
-            }
-          ],
-          "where_predicates": []
-        },
-        "fields_stripped": true
-      }
-    },
-    "0:0": {
-      "crate_id": 0,
-      "name": "structs",
-      "source": {
-        "filename": "$TEST_BASE_DIR/structs.rs",
-        "begin": [
-          1,
-          0
-        ],
-        "end": [
-          17,
-          1
-        ]
-      },
-      "visibility": "public",
-      "docs": "",
-      "links": {},
-      "attrs": [],
-      "deprecation": null,
-      "kind": "module",
-      "inner": {
-        "is_crate": true,
-        "items": [
-          "0:4",
-          "0:5",
-          "0:9",
-          "0:11",
-          "0:15"
-        ]
-      }
-    },
-    "0:13": {
-      "crate_id": 0,
-      "name": "num",
-      "source": {
-        "filename": "$TEST_BASE_DIR/structs.rs",
-        "begin": [
-          10,
-          4
-        ],
-        "end": [
-          10,
-          12
-        ]
-      },
-      "visibility": "default",
-      "docs": "",
-      "links": {},
-      "attrs": [],
-      "deprecation": null,
-      "kind": "struct_field",
-      "inner": {
-        "kind": "primitive",
-        "inner": "u32"
-      }
-    },
-    "0:5": {
-      "crate_id": 0,
-      "name": "Tuple",
-      "source": {
-        "filename": "$TEST_BASE_DIR/structs.rs",
-        "begin": [
-          5,
-          0
-        ],
-        "end": [
-          5,
-          30
-        ]
-      },
-      "visibility": "public",
-      "docs": "",
-      "links": {},
-      "attrs": [],
-      "deprecation": null,
-      "kind": "struct",
-      "inner": {
-        "struct_type": "tuple",
-        "generics": {
-          "params": [],
-          "where_predicates": []
-        },
-        "fields_stripped": true
-      }
-    },
-    "0:4": {
-      "crate_id": 0,
-      "name": "PlainEmpty",
-      "source": {
-        "filename": "$TEST_BASE_DIR/structs.rs",
-        "begin": [
-          3,
-          0
-        ],
-        "end": [
-          3,
-          24
-        ]
-      },
-      "visibility": "public",
-      "docs": "",
-      "links": {},
-      "attrs": [],
-      "deprecation": null,
-      "kind": "struct",
-      "inner": {
-        "struct_type": "plain",
-        "generics": {
-          "params": [],
-          "where_predicates": []
-        },
-        "fields_stripped": false,
-        "fields": []
-      }
-    },
-    "0:7": {
-      "crate_id": 0,
-      "name": "0",
-      "source": {
-        "filename": "$TEST_BASE_DIR/structs.rs",
-        "begin": [
-          5,
-          17
-        ],
-        "end": [
-          5,
-          20
-        ]
-      },
-      "visibility": "default",
-      "docs": "",
-      "links": {},
-      "attrs": [],
-      "deprecation": null,
-      "kind": "struct_field",
-      "inner": {
-        "kind": "primitive",
-        "inner": "u32"
-      }
-    }
-  },
-  "paths": {
-    "5:4322": {
-      "crate_id": 5,
-      "path": [
-        "alloc",
-        "vec",
-        "Vec"
-      ],
-      "kind": "struct"
-    },
-    "5:5035": {
-      "crate_id": 5,
-      "path": [
-        "alloc",
-        "string",
-        "String"
-      ],
-      "kind": "struct"
-    },
-    "1:6600": {
-      "crate_id": 1,
-      "path": [
-        "std",
-        "collections",
-        "hash",
-        "map",
-        "HashMap"
-      ],
-      "kind": "struct"
-    }
-  },
-  "external_crates": {
-    "1": {
-      "name": "std"
-    },
-    "5": {
-      "name": "alloc"
-    }
-  },
-  "format_version": 1
-}
diff --git a/src/test/rustdoc-json/structs.rs b/src/test/rustdoc-json/structs.rs
deleted file mode 100644
index 43fc4743503..00000000000
--- a/src/test/rustdoc-json/structs.rs
+++ /dev/null
@@ -1,17 +0,0 @@
-use std::collections::HashMap;
-
-pub struct PlainEmpty {}
-
-pub struct Tuple(u32, String);
-
-pub struct Unit;
-
-pub struct WithPrimitives<'a> {
-    num: u32,
-    s: &'a str,
-}
-
-pub struct WithGenerics<T, U> {
-    stuff: Vec<T>,
-    things: HashMap<U, U>,
-}
diff --git a/src/test/rustdoc-json/structs/plain_empty.rs b/src/test/rustdoc-json/structs/plain_empty.rs
new file mode 100644
index 00000000000..a251caf4ba9
--- /dev/null
+++ b/src/test/rustdoc-json/structs/plain_empty.rs
@@ -0,0 +1,6 @@
+// @has plain_empty.json "$.index[*][?(@.name=='PlainEmpty')].visibility" \"public\"
+// @has - "$.index[*][?(@.name=='PlainEmpty')].kind" \"struct\"
+// @has - "$.index[*][?(@.name=='PlainEmpty')].inner.struct_type" \"plain\"
+// @has - "$.index[*][?(@.name=='PlainEmpty')].inner.fields_stripped" false
+// @has - "$.index[*][?(@.name=='PlainEmpty')].inner.fields" []
+pub struct PlainEmpty {}
diff --git a/src/test/rustdoc-json/structs/tuple.rs b/src/test/rustdoc-json/structs/tuple.rs
new file mode 100644
index 00000000000..4e510b39825
--- /dev/null
+++ b/src/test/rustdoc-json/structs/tuple.rs
@@ -0,0 +1,5 @@
+// @has tuple.json "$.index[*][?(@.name=='Tuple')].visibility" \"public\"
+// @has - "$.index[*][?(@.name=='Tuple')].kind" \"struct\"
+// @has - "$.index[*][?(@.name=='Tuple')].inner.struct_type" \"tuple\"
+// @has - "$.index[*][?(@.name=='Tuple')].inner.fields_stripped" true
+pub struct Tuple(u32, String);
diff --git a/src/test/rustdoc-json/structs/unit.rs b/src/test/rustdoc-json/structs/unit.rs
new file mode 100644
index 00000000000..559d3068de6
--- /dev/null
+++ b/src/test/rustdoc-json/structs/unit.rs
@@ -0,0 +1,5 @@
+// @has unit.json "$.index[*][?(@.name=='Unit')].visibility" \"public\"
+// @has - "$.index[*][?(@.name=='Unit')].kind" \"struct\"
+// @has - "$.index[*][?(@.name=='Unit')].inner.struct_type" \"unit\"
+// @has - "$.index[*][?(@.name=='Unit')].inner.fields" []
+pub struct Unit;
diff --git a/src/test/rustdoc-json/structs/with_generics.rs b/src/test/rustdoc-json/structs/with_generics.rs
new file mode 100644
index 00000000000..65cfe7effa5
--- /dev/null
+++ b/src/test/rustdoc-json/structs/with_generics.rs
@@ -0,0 +1,14 @@
+use std::collections::HashMap;
+
+// @has with_generics.json "$.index[*][?(@.name=='WithGenerics')].visibility" \"public\"
+// @has - "$.index[*][?(@.name=='WithGenerics')].kind" \"struct\"
+// @has - "$.index[*][?(@.name=='WithGenerics')].inner.generics.params[0].name" \"T\"
+// @has - "$.index[*][?(@.name=='WithGenerics')].inner.generics.params[0].kind.type"
+// @has - "$.index[*][?(@.name=='WithGenerics')].inner.generics.params[1].name" \"U\"
+// @has - "$.index[*][?(@.name=='WithGenerics')].inner.generics.params[1].kind.type"
+// @has - "$.index[*][?(@.name=='WithGenerics')].inner.struct_type" \"plain\"
+// @has - "$.index[*][?(@.name=='WithGenerics')].inner.fields_stripped" true
+pub struct WithGenerics<T, U> {
+    stuff: Vec<T>,
+    things: HashMap<U, U>,
+}
diff --git a/src/test/rustdoc-json/structs/with_primitives.rs b/src/test/rustdoc-json/structs/with_primitives.rs
new file mode 100644
index 00000000000..ea98676863b
--- /dev/null
+++ b/src/test/rustdoc-json/structs/with_primitives.rs
@@ -0,0 +1,10 @@
+// @has with_primitives.json "$.index[*][?(@.name=='WithPrimitives')].visibility" \"public\"
+// @has - "$.index[*][?(@.name=='WithPrimitives')].kind" \"struct\"
+// @has - "$.index[*][?(@.name=='WithPrimitives')].inner.generics.params[0].name" \"\'a\"
+// @has - "$.index[*][?(@.name=='WithPrimitives')].inner.generics.params[0].kind" \"lifetime\"
+// @has - "$.index[*][?(@.name=='WithPrimitives')].inner.struct_type" \"plain\"
+// @has - "$.index[*][?(@.name=='WithPrimitives')].inner.fields_stripped" true
+pub struct WithPrimitives<'a> {
+    num: u32,
+    s: &'a str,
+}
diff --git a/src/tools/compiletest/src/common.rs b/src/tools/compiletest/src/common.rs
index 43dbaeb4655..5424889a838 100644
--- a/src/tools/compiletest/src/common.rs
+++ b/src/tools/compiletest/src/common.rs
@@ -198,6 +198,9 @@ pub struct Config {
     /// The Python executable to use for htmldocck.
     pub docck_python: String,
 
+    /// The jsondocck executable.
+    pub jsondocck_path: Option<String>,
+
     /// The LLVM `FileCheck` binary path.
     pub llvm_filecheck: Option<PathBuf>,
 
diff --git a/src/tools/compiletest/src/header/tests.rs b/src/tools/compiletest/src/header/tests.rs
index 4bcbd89f095..ec99fde0df9 100644
--- a/src/tools/compiletest/src/header/tests.rs
+++ b/src/tools/compiletest/src/header/tests.rs
@@ -45,6 +45,7 @@ fn config() -> Config {
         "--rustc-path=",
         "--lldb-python=",
         "--docck-python=",
+        "--jsondocck-path=",
         "--src-base=",
         "--build-base=",
         "--stage-id=stage2",
diff --git a/src/tools/compiletest/src/main.rs b/src/tools/compiletest/src/main.rs
index aefcfe222e5..688cf930033 100644
--- a/src/tools/compiletest/src/main.rs
+++ b/src/tools/compiletest/src/main.rs
@@ -60,6 +60,7 @@ pub fn parse_config(args: Vec<String>) -> Config {
         .optopt("", "rust-demangler-path", "path to rust-demangler to use in tests", "PATH")
         .reqopt("", "lldb-python", "path to python to use for doc tests", "PATH")
         .reqopt("", "docck-python", "path to python to use for doc tests", "PATH")
+        .optopt("", "jsondocck-path", "path to jsondocck to use for doc tests", "PATH")
         .optopt("", "valgrind-path", "path to Valgrind executable for Valgrind tests", "PROGRAM")
         .optflag("", "force-valgrind", "fail if Valgrind tests cannot be run under Valgrind")
         .optopt("", "run-clang-based-tests-with", "path to Clang executable", "PATH")
@@ -207,6 +208,7 @@ pub fn parse_config(args: Vec<String>) -> Config {
         rust_demangler_path: matches.opt_str("rust-demangler-path").map(PathBuf::from),
         lldb_python: matches.opt_str("lldb-python").unwrap(),
         docck_python: matches.opt_str("docck-python").unwrap(),
+        jsondocck_path: matches.opt_str("jsondocck-path"),
         valgrind_path: matches.opt_str("valgrind-path"),
         force_valgrind: matches.opt_present("force-valgrind"),
         run_clang_based_tests_with: matches.opt_str("run-clang-based-tests-with"),
diff --git a/src/tools/compiletest/src/runtest.rs b/src/tools/compiletest/src/runtest.rs
index 9f31b3ae1b1..5608ff98417 100644
--- a/src/tools/compiletest/src/runtest.rs
+++ b/src/tools/compiletest/src/runtest.rs
@@ -2487,31 +2487,31 @@ impl<'test> TestCx<'test> {
         }
 
         let root = self.config.find_rust_src_root().unwrap();
+        let mut json_out = out_dir.join(self.testpaths.file.file_stem().unwrap());
+        json_out.set_extension("json");
+        let res = self.cmd2procres(
+            Command::new(self.config.jsondocck_path.as_ref().unwrap())
+                .arg("--doc-dir")
+                .arg(root.join(&out_dir))
+                .arg("--template")
+                .arg(&self.testpaths.file),
+        );
+
+        if !res.status.success() {
+            self.fatal_proc_rec("jsondocck failed!", &res)
+        }
+
         let mut json_out = out_dir.join(self.testpaths.file.file_stem().unwrap());
         json_out.set_extension("json");
         let res = self.cmd2procres(
             Command::new(&self.config.docck_python)
-                .arg(root.join("src/test/rustdoc-json/check_missing_items.py"))
+                .arg(root.join("src/etc/check_missing_items.py"))
                 .arg(&json_out),
         );
 
         if !res.status.success() {
             self.fatal_proc_rec("check_missing_items failed!", &res);
         }
-
-        let mut expected = self.testpaths.file.clone();
-        expected.set_extension("expected");
-        let res = self.cmd2procres(
-            Command::new(&self.config.docck_python)
-                .arg(root.join("src/test/rustdoc-json/compare.py"))
-                .arg(&expected)
-                .arg(&json_out)
-                .arg(&expected.parent().unwrap()),
-        );
-
-        if !res.status.success() {
-            self.fatal_proc_rec("compare failed!", &res);
-        }
     }
 
     fn get_lines<P: AsRef<Path>>(
diff --git a/src/tools/jsondocck/Cargo.toml b/src/tools/jsondocck/Cargo.toml
new file mode 100644
index 00000000000..97052ef58d6
--- /dev/null
+++ b/src/tools/jsondocck/Cargo.toml
@@ -0,0 +1,14 @@
+[package]
+name = "jsondocck"
+version = "0.1.0"
+authors = ["Rune Tynan <runetynan@gmail.com>"]
+edition = "2018"
+
+[dependencies]
+jsonpath_lib = "0.2"
+getopts = "0.2"
+regex = "1.4"
+lazy_static = "1.4"
+shlex = "0.1"
+serde = "1.0"
+serde_json = "1.0"
diff --git a/src/tools/jsondocck/src/cache.rs b/src/tools/jsondocck/src/cache.rs
new file mode 100644
index 00000000000..b742f0eb3ee
--- /dev/null
+++ b/src/tools/jsondocck/src/cache.rs
@@ -0,0 +1,69 @@
+use crate::error::CkError;
+use serde_json::Value;
+use std::collections::HashMap;
+use std::path::{Path, PathBuf};
+use std::{fs, io};
+
+#[derive(Debug)]
+pub struct Cache {
+    root: PathBuf,
+    files: HashMap<PathBuf, String>,
+    values: HashMap<PathBuf, Value>,
+    last_path: Option<PathBuf>,
+}
+
+impl Cache {
+    /// Create a new cache, used to read files only once and otherwise store their contents.
+    pub fn new(doc_dir: &str) -> Cache {
+        Cache {
+            root: Path::new(doc_dir).to_owned(),
+            files: HashMap::new(),
+            values: HashMap::new(),
+            last_path: None,
+        }
+    }
+
+    fn resolve_path(&mut self, path: &String) -> PathBuf {
+        if path != "-" {
+            let resolve = self.root.join(path);
+            self.last_path = Some(resolve.clone());
+            resolve
+        } else {
+            self.last_path.as_ref().unwrap().clone()
+        }
+    }
+
+    fn read_file(&mut self, path: PathBuf) -> Result<String, io::Error> {
+        if let Some(f) = self.files.get(&path) {
+            return Ok(f.clone());
+        }
+
+        let file = fs::read_to_string(&path)?;
+
+        self.files.insert(path, file.clone());
+
+        Ok(file)
+    }
+
+    /// Get the text from a file. If called multiple times, the file will only be read once
+    pub fn get_file(&mut self, path: &String) -> Result<String, io::Error> {
+        let path = self.resolve_path(path);
+        self.read_file(path)
+    }
+
+    /// Parse the JSON from a file. If called multiple times, the file will only be read once.
+    pub fn get_value(&mut self, path: &String) -> Result<Value, CkError> {
+        let path = self.resolve_path(path);
+
+        if let Some(v) = self.values.get(&path) {
+            return Ok(v.clone());
+        }
+
+        let content = self.read_file(path.clone())?;
+        let val = serde_json::from_str::<Value>(&content)?;
+
+        self.values.insert(path, val.clone());
+
+        Ok(val)
+    }
+}
diff --git a/src/tools/jsondocck/src/config.rs b/src/tools/jsondocck/src/config.rs
new file mode 100644
index 00000000000..9b3ba3f3fbe
--- /dev/null
+++ b/src/tools/jsondocck/src/config.rs
@@ -0,0 +1,37 @@
+use getopts::Options;
+
+#[derive(Debug)]
+pub struct Config {
+    /// The directory documentation output was generated in
+    pub doc_dir: String,
+    /// The file documentation was generated for, with docck commands to check
+    pub template: String,
+}
+
+/// Create a Config from a vector of command-line arguments
+pub fn parse_config(args: Vec<String>) -> Config {
+    let mut opts = Options::new();
+    opts.reqopt("", "doc-dir", "Path to the documentation directory", "PATH")
+        .reqopt("", "template", "Path to the template file", "PATH")
+        .optflag("h", "help", "show this message");
+
+    let (argv0, args_) = args.split_first().unwrap();
+    if args.len() == 1 {
+        let message = format!("Usage: {} <doc-dir> <template>", argv0);
+        println!("{}", opts.usage(&message));
+        std::process::exit(1);
+    }
+
+    let matches = opts.parse(args_).unwrap();
+
+    if matches.opt_present("h") || matches.opt_present("help") {
+        let message = format!("Usage: {} <doc-dir> <template>", argv0);
+        println!("{}", opts.usage(&message));
+        std::process::exit(1);
+    }
+
+    Config {
+        doc_dir: matches.opt_str("doc-dir").unwrap(),
+        template: matches.opt_str("template").unwrap(),
+    }
+}
diff --git a/src/tools/jsondocck/src/error.rs b/src/tools/jsondocck/src/error.rs
new file mode 100644
index 00000000000..53b9af2874b
--- /dev/null
+++ b/src/tools/jsondocck/src/error.rs
@@ -0,0 +1,28 @@
+use crate::Command;
+use std::error::Error;
+use std::fmt;
+
+#[derive(Debug)]
+pub enum CkError {
+    /// A check failed. File didn't exist or failed to match the command
+    FailedCheck(String, Command),
+    /// An error triggered by some other error
+    Induced(Box<dyn Error>),
+}
+
+impl fmt::Display for CkError {
+    fn fmt(&self, f: &mut fmt::Formatter<'_>) -> fmt::Result {
+        match self {
+            CkError::FailedCheck(msg, cmd) => {
+                write!(f, "Failed check: {} on line {}", msg, cmd.lineno)
+            }
+            CkError::Induced(err) => write!(f, "Check failed: {}", err),
+        }
+    }
+}
+
+impl<T: Error + 'static> From<T> for CkError {
+    fn from(err: T) -> CkError {
+        CkError::Induced(Box::new(err))
+    }
+}
diff --git a/src/tools/jsondocck/src/main.rs b/src/tools/jsondocck/src/main.rs
new file mode 100644
index 00000000000..29131f686a9
--- /dev/null
+++ b/src/tools/jsondocck/src/main.rs
@@ -0,0 +1,234 @@
+use jsonpath_lib::select;
+use lazy_static::lazy_static;
+use regex::{Regex, RegexBuilder};
+use serde_json::Value;
+use std::{env, fmt, fs};
+
+mod cache;
+mod config;
+mod error;
+
+use cache::Cache;
+use config::parse_config;
+use error::CkError;
+
+fn main() -> Result<(), String> {
+    let config = parse_config(env::args().collect());
+
+    let mut failed = Vec::new();
+    let mut cache = Cache::new(&config.doc_dir);
+    let commands = get_commands(&config.template)
+        .map_err(|_| format!("Jsondocck failed for {}", &config.template))?;
+
+    for command in commands {
+        if let Err(e) = check_command(command, &mut cache) {
+            failed.push(e);
+        }
+    }
+
+    if failed.is_empty() {
+        Ok(())
+    } else {
+        for i in failed {
+            eprintln!("{}", i);
+        }
+        Err(format!("Jsondocck failed for {}", &config.template))
+    }
+}
+
+#[derive(Debug)]
+pub struct Command {
+    negated: bool,
+    kind: CommandKind,
+    args: Vec<String>,
+    lineno: usize,
+}
+
+#[derive(Debug)]
+pub enum CommandKind {
+    Has,
+    Count,
+}
+
+impl CommandKind {
+    fn validate(&self, args: &[String], command_num: usize, lineno: usize) -> bool {
+        let count = match self {
+            CommandKind::Has => (1..=3).contains(&args.len()),
+            CommandKind::Count => 3 == args.len(),
+        };
+
+        if !count {
+            print_err(&format!("Incorrect number of arguments to `@{}`", self), lineno);
+            return false;
+        }
+
+        if args[0] == "-" && command_num == 0 {
+            print_err(&format!("Tried to use the previous path in the first command"), lineno);
+            return false;
+        }
+
+        if let CommandKind::Count = self {
+            if args[2].parse::<usize>().is_err() {
+                print_err(&format!("Third argument to @count must be a valid usize"), lineno);
+                return false;
+            }
+        }
+
+        true
+    }
+}
+
+impl fmt::Display for CommandKind {
+    fn fmt(&self, f: &mut fmt::Formatter<'_>) -> fmt::Result {
+        let text = match self {
+            CommandKind::Has => "has",
+            CommandKind::Count => "count",
+        };
+        write!(f, "{}", text)
+    }
+}
+
+lazy_static! {
+    static ref LINE_PATTERN: Regex = RegexBuilder::new(
+        r#"
+        \s(?P<invalid>!?)@(?P<negated>!?)
+        (?P<cmd>[A-Za-z]+(?:-[A-Za-z]+)*)
+        (?P<args>.*)$
+    "#
+    )
+    .ignore_whitespace(true)
+    .unicode(true)
+    .build()
+    .unwrap();
+}
+
+fn print_err(msg: &str, lineno: usize) {
+    eprintln!("Invalid command: {} on line {}", msg, lineno)
+}
+
+/// Get a list of commands from a file. Does the work of ensuring the commands
+/// are syntactically valid.
+fn get_commands(template: &str) -> Result<Vec<Command>, ()> {
+    let mut commands = Vec::new();
+    let mut errors = false;
+    let file = fs::read_to_string(template).unwrap();
+
+    for (lineno, line) in file.split('\n').enumerate() {
+        let lineno = lineno + 1;
+
+        let cap = match LINE_PATTERN.captures(line) {
+            Some(c) => c,
+            None => continue,
+        };
+
+        let negated = cap.name("negated").unwrap().as_str() == "!";
+        let cmd = cap.name("cmd").unwrap().as_str();
+
+        let cmd = match cmd {
+            "has" => CommandKind::Has,
+            "count" => CommandKind::Count,
+            _ => {
+                print_err(&format!("Unrecognized command name `@{}`", cmd), lineno);
+                errors = true;
+                continue;
+            }
+        };
+
+        if let Some(m) = cap.name("invalid") {
+            if m.as_str() == "!" {
+                print_err(
+                    &format!(
+                        "`!@{0}{1}`, (help: try with `@!{1}`)",
+                        if negated { "!" } else { "" },
+                        cmd,
+                    ),
+                    lineno,
+                );
+                errors = true;
+                continue;
+            }
+        }
+
+        let args = cap.name("args").map_or(vec![], |m| shlex::split(m.as_str()).unwrap());
+
+        if !cmd.validate(&args, commands.len(), lineno) {
+            errors = true;
+            continue;
+        }
+
+        commands.push(Command { negated, kind: cmd, args, lineno })
+    }
+
+    if !errors { Ok(commands) } else { Err(()) }
+}
+
+/// Performs the actual work of ensuring a command passes. Generally assumes the command
+/// is syntactically valid.
+fn check_command(command: Command, cache: &mut Cache) -> Result<(), CkError> {
+    let result = match command.kind {
+        CommandKind::Has => {
+            match command.args.len() {
+                // @has <path> = file existence
+                1 => cache.get_file(&command.args[0]).is_ok(),
+                // @has <path> <jsonpath> = check path exists
+                2 => {
+                    let val = cache.get_value(&command.args[0])?;
+
+                    match select(&val, &command.args[1]) {
+                        Ok(results) => !results.is_empty(),
+                        Err(_) => false,
+                    }
+                }
+                // @has <path> <jsonpath> <value> = check *any* item matched by path equals value
+                3 => {
+                    let val = cache.get_value(&command.args[0])?;
+                    match select(&val, &command.args[1]) {
+                        Ok(results) => {
+                            let pat: Value = serde_json::from_str(&command.args[2]).unwrap();
+
+                            !results.is_empty() && results.into_iter().any(|val| *val == pat)
+                        }
+                        Err(_) => false,
+                    }
+                }
+                _ => unreachable!(),
+            }
+        }
+        CommandKind::Count => {
+            // @count <path> <jsonpath> <count> = Check that the jsonpath matches exactly [count] times
+            assert_eq!(command.args.len(), 3);
+            let expected: usize = command.args[2].parse().unwrap();
+
+            let val = cache.get_value(&command.args[0])?;
+            match select(&val, &command.args[1]) {
+                Ok(results) => results.len() == expected,
+                Err(_) => false,
+            }
+        }
+    };
+
+    if result == command.negated {
+        if command.negated {
+            Err(CkError::FailedCheck(
+                format!(
+                    "`@!{} {}` matched when it shouldn't",
+                    command.kind,
+                    command.args.join(" ")
+                ),
+                command,
+            ))
+        } else {
+            // FIXME: In the future, try 'peeling back' each step, and see at what level the match failed
+            Err(CkError::FailedCheck(
+                format!(
+                    "`@{} {}` didn't match when it should",
+                    command.kind,
+                    command.args.join(" ")
+                ),
+                command,
+            ))
+        }
+    } else {
+        Ok(())
+    }
+}