diff --git a/doc/api/assert.md b/doc/api/assert.md
index 585a9dff4b3e48..277f29880d5b24 100644
--- a/doc/api/assert.md
+++ b/doc/api/assert.md
@@ -425,6 +425,42 @@ parameter is undefined, a default error message is assigned. If the `message`
 parameter is an instance of an [`Error`][] then it will be thrown instead of the
 `AssertionError`.
 
+## `assert.doesNotMatch(string, regexp[, message])`
+<!-- YAML
+added: REPLACEME
+-->
+
+* `string` {string}
+* `regexp` {RegExp}
+* `message` {string|Error}
+
+> Stability: 1 - Experimental
+
+Expects the `string` input not to match the regular expression.
+
+This feature is currently experimental and the name might change or it might be
+completely removed again.
+
+```js
+const assert = require('assert').strict;
+
+assert.doesNotMatch('I will fail', /fail/);
+// AssertionError [ERR_ASSERTION]: The input was expected to not match the ...
+
+assert.doesNotMatch(123, /pass/);
+// AssertionError [ERR_ASSERTION]: The "string" argument must be of type string.
+
+assert.doesNotMatch('I will pass', /different/);
+// OK
+```
+
+If the values do match, or if the `string` argument is of another type than
+`string`, an [`AssertionError`][] is thrown with a `message` property set equal
+to the value of the `message` parameter. If the `message` parameter is
+undefined, a default error message is assigned. If the `message` parameter is an
+instance of an [`Error`][] then it will be thrown instead of the
+[`AssertionError`][].
+
 ## `assert.doesNotReject(asyncFn[, error][, message])`
 <!-- YAML
 added: v10.0.0
@@ -728,6 +764,42 @@ let err;
 //     at errorFrame
 ```
 
+## `assert.match(string, regexp[, message])`
+<!-- YAML
+added: REPLACEME
+-->
+
+* `string` {string}
+* `regexp` {RegExp}
+* `message` {string|Error}
+
+> Stability: 1 - Experimental
+
+Expects the `string` input to match the regular expression.
+
+This feature is currently experimental and the name might change or it might be
+completely removed again.
+
+```js
+const assert = require('assert').strict;
+
+assert.match('I will fail', /pass/);
+// AssertionError [ERR_ASSERTION]: The input did not match the regular ...
+
+assert.match(123, /pass/);
+// AssertionError [ERR_ASSERTION]: The "string" argument must be of type string.
+
+assert.match('I will pass', /pass/);
+// OK
+```
+
+If the values do not match, or if the `string` argument is of another type than
+`string`, an [`AssertionError`][] is thrown with a `message` property set equal
+to the value of the `message` parameter. If the `message` parameter is
+undefined, a default error message is assigned. If the `message` parameter is an
+instance of an [`Error`][] then it will be thrown instead of the
+[`AssertionError`][].
+
 ## `assert.notDeepEqual(actual, expected[, message])`
 <!-- YAML
 added: v0.1.21
diff --git a/lib/assert.js b/lib/assert.js
index 52523db3948ca7..f37166be9c6798 100644
--- a/lib/assert.js
+++ b/lib/assert.js
@@ -27,6 +27,7 @@ const {
   ObjectKeys,
   ObjectPrototypeIsPrototypeOf,
   Map,
+  RegExpPrototypeTest,
 } = primordials;
 
 const { Buffer } = require('buffer');
@@ -533,7 +534,7 @@ class Comparison {
         if (actual !== undefined &&
             typeof actual[key] === 'string' &&
             isRegExp(obj[key]) &&
-            obj[key].test(actual[key])) {
+            RegExpPrototypeTest(obj[key], actual[key])) {
           this[key] = actual[key];
         } else {
           this[key] = obj[key];
@@ -579,7 +580,7 @@ function expectedException(actual, expected, message, fn) {
     // Handle regular expressions.
     if (isRegExp(expected)) {
       const str = String(actual);
-      if (expected.test(str))
+      if (RegExpPrototypeTest(expected, str))
         return;
 
       if (!message) {
@@ -614,7 +615,7 @@ function expectedException(actual, expected, message, fn) {
       for (const key of keys) {
         if (typeof actual[key] === 'string' &&
             isRegExp(expected[key]) &&
-            expected[key].test(actual[key])) {
+            RegExpPrototypeTest(expected[key], actual[key])) {
           continue;
         }
         compareExceptionKey(actual, expected, key, message, keys, fn);
@@ -751,7 +752,7 @@ function hasMatchingError(actual, expected) {
   if (typeof expected !== 'function') {
     if (isRegExp(expected)) {
       const str = String(actual);
-      return expected.test(str);
+      return RegExpPrototypeTest(expected, str);
     }
     throw new ERR_INVALID_ARG_TYPE(
       'expected', ['Function', 'RegExp'], expected
@@ -856,6 +857,49 @@ assert.ifError = function ifError(err) {
   }
 };
 
+function internalMatch(string, regexp, message, fn) {
+  if (!isRegExp(regexp)) {
+    throw new ERR_INVALID_ARG_TYPE(
+      'regexp', 'RegExp', regexp
+    );
+  }
+  const match = fn.name === 'match';
+  if (typeof string !== 'string' ||
+      RegExpPrototypeTest(regexp, string) !== match) {
+    if (message instanceof Error) {
+      throw message;
+    }
+
+    const generatedMessage = !message;
+
+    // 'The input was expected to not match the regular expression ' +
+    message = message || (typeof string !== 'string' ?
+      'The "string" argument must be of type string. Received type ' +
+        `${typeof string} (${inspect(string)})` :
+      (match ?
+        'The input did not match the regular expression ' :
+        'The input was expected to not match the regular expression ') +
+          `${inspect(regexp)}. Input:\n\n${inspect(string)}\n`);
+    const err = new AssertionError({
+      actual: string,
+      expected: regexp,
+      message,
+      operator: fn.name,
+      stackStartFn: fn
+    });
+    err.generatedMessage = generatedMessage;
+    throw err;
+  }
+}
+
+assert.match = function match(string, regexp, message) {
+  internalMatch(string, regexp, message, match);
+};
+
+assert.doesNotMatch = function doesNotMatch(string, regexp, message) {
+  internalMatch(string, regexp, message, doesNotMatch);
+};
+
 // Expose a strict only variant of assert
 function strict(...args) {
   innerOk(strict, args.length, ...args);
diff --git a/test/parallel/test-assert.js b/test/parallel/test-assert.js
index f0204d52f51b5b..27421d2373eab1 100644
--- a/test/parallel/test-assert.js
+++ b/test/parallel/test-assert.js
@@ -1301,3 +1301,103 @@ assert.throws(
     assert(!err2.stack.includes('hidden'));
   })();
 }
+
+// Multiple assert.match() tests.
+{
+  assert.throws(
+    () => assert.match(/abc/, 'string'),
+    {
+      code: 'ERR_INVALID_ARG_TYPE',
+      message: 'The "regexp" argument must be an instance of RegExp. ' +
+               "Received type string ('string')"
+    }
+  );
+  assert.throws(
+    () => assert.match('string', /abc/),
+    {
+      actual: 'string',
+      expected: /abc/,
+      operator: 'match',
+      message: 'The input did not match the regular expression /abc/. ' +
+               "Input:\n\n'string'\n",
+      generatedMessage: true
+    }
+  );
+  assert.throws(
+    () => assert.match('string', /abc/, 'foobar'),
+    {
+      actual: 'string',
+      expected: /abc/,
+      operator: 'match',
+      message: 'foobar',
+      generatedMessage: false
+    }
+  );
+  const errorMessage = new RangeError('foobar');
+  assert.throws(
+    () => assert.match('string', /abc/, errorMessage),
+    errorMessage
+  );
+  assert.throws(
+    () => assert.match({ abc: 123 }, /abc/),
+    {
+      actual: { abc: 123 },
+      expected: /abc/,
+      operator: 'match',
+      message: 'The "string" argument must be of type string. ' +
+               'Received type object ({ abc: 123 })',
+      generatedMessage: true
+    }
+  );
+  assert.match('I will pass', /pass$/);
+}
+
+// Multiple assert.doesNotMatch() tests.
+{
+  assert.throws(
+    () => assert.doesNotMatch(/abc/, 'string'),
+    {
+      code: 'ERR_INVALID_ARG_TYPE',
+      message: 'The "regexp" argument must be an instance of RegExp. ' +
+               "Received type string ('string')"
+    }
+  );
+  assert.throws(
+    () => assert.doesNotMatch('string', /string/),
+    {
+      actual: 'string',
+      expected: /string/,
+      operator: 'doesNotMatch',
+      message: 'The input was expected to not match the regular expression ' +
+               "/string/. Input:\n\n'string'\n",
+      generatedMessage: true
+    }
+  );
+  assert.throws(
+    () => assert.doesNotMatch('string', /string/, 'foobar'),
+    {
+      actual: 'string',
+      expected: /string/,
+      operator: 'doesNotMatch',
+      message: 'foobar',
+      generatedMessage: false
+    }
+  );
+  const errorMessage = new RangeError('foobar');
+  assert.throws(
+    () => assert.doesNotMatch('string', /string/, errorMessage),
+    errorMessage
+  );
+  assert.throws(
+    () => assert.doesNotMatch({ abc: 123 }, /abc/),
+    {
+      actual: { abc: 123 },
+      expected: /abc/,
+      operator: 'doesNotMatch',
+      message: 'The "string" argument must be of type string. ' +
+               'Received type object ({ abc: 123 })',
+      generatedMessage: true
+    }
+  );
+  assert.doesNotMatch('I will pass', /different$/);
+}