diff --git a/CHANGELOG.md b/CHANGELOG.md
index 865d3a5fca39..32a04647a3bb 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -14,6 +14,7 @@
 - `[expect]` `toEqual` no longer tries to compare non-enumerable symbolic properties, to be consistent with non-symbolic properties. ([#6398](https://github.com/facebook/jest/pull/6398))
 - `[jest-util]` `console.timeEnd` now properly log elapsed time in milliseconds. ([#6456](https://github.com/facebook/jest/pull/6456))
 - `[jest-mock]` Fix `MockNativeMethods` access in react-native `jest.mock()` ([#6505](https://github.com/facebook/jest/pull/6505))
+- `[jest-regex-util]` Improve handling already escaped path separators on Windows ([#6523](https://github.com/facebook/jest/pull/6523))
 
 ### Chore & Maintenance
 
diff --git a/packages/jest-regex-util/src/__tests__/index.test.js b/packages/jest-regex-util/src/__tests__/index.test.js
index a15eaa77d1e6..077e6a247445 100644
--- a/packages/jest-regex-util/src/__tests__/index.test.js
+++ b/packages/jest-regex-util/src/__tests__/index.test.js
@@ -31,17 +31,23 @@ describe('replacePathSepForRegex()', () => {
 
     it('should not escape an escaped dot', () => {
       expect(replacePathSepForRegex('a\\.dotfile')).toBe('a\\.dotfile');
-
-      // If we expect Windows path separators to be escaped, one would expect
-      // the regular expression "\\\." to be unescaped as "\.". This is not the
-      // current behavior.
-      expect(replacePathSepForRegex('a\\\\\\.dotfile')).toBe(
-        'a\\\\\\\\\\.dotfile',
-      );
+      expect(replacePathSepForRegex('a\\\\\\.dotfile')).toBe('a\\\\\\.dotfile');
     });
 
     it('should not escape an escaped regexp symbol', () => {
       expect(replacePathSepForRegex('b\\(86')).toBe('b\\(86');
     });
+
+    it('should escape Windows path separators inside groups', () => {
+      expect(replacePathSepForRegex('[/\\\\]')).toBe('[\\\\\\\\]');
+    });
+
+    it('should escape Windows path separator at the beginning', () => {
+      expect(replacePathSepForRegex('\\a')).toBe('\\\\a');
+    });
+
+    it('should not escape several already escaped path separators', () => {
+      expect(replacePathSepForRegex('\\\\\\\\')).toBe('\\\\\\\\');
+    });
   });
 });
diff --git a/packages/jest-regex-util/src/index.js b/packages/jest-regex-util/src/index.js
index 635a1931f0ff..cb8bf41b1ecb 100644
--- a/packages/jest-regex-util/src/index.js
+++ b/packages/jest-regex-util/src/index.js
@@ -23,7 +23,10 @@ export const escapeStrForRegex = (string: string) =>
 
 export const replacePathSepForRegex = (string: string) => {
   if (path.sep === '\\') {
-    return string.replace(/(\/|\\(?![[\]{}()*+?.^$|]))/g, '\\\\');
+    return string.replace(
+      /(\/|(.)?\\(?![[\]{}()*+?.^$|\\]))/g,
+      (_match, p1, p2) => (p2 && p2 !== '\\' ? p2 + '\\\\' : '\\\\'),
+    );
   }
   return string;
 };