diff --git a/playwright/_impl/_glob.py b/playwright/_impl/_glob.py
new file mode 100644
index 000000000..2d899a789
--- /dev/null
+++ b/playwright/_impl/_glob.py
@@ -0,0 +1,68 @@
+# Copyright (c) Microsoft Corporation.
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+# http://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+import re
+
+#  https://developer.mozilla.org/en-US/docs/Web/JavaScript/Guide/Regular_expressions#escaping
+escaped_chars = {"$", "^", "+", ".", "*", "(", ")", "|", "\\", "?", "{", "}", "[", "]"}
+
+
+def glob_to_regex(glob: str) -> "re.Pattern[str]":
+    tokens = ["^"]
+    in_group = False
+
+    i = 0
+    while i < len(glob):
+        c = glob[i]
+        if c == "\\" and i + 1 < len(glob):
+            char = glob[i + 1]
+            tokens.append("\\" + char if char in escaped_chars else char)
+            i += 1
+        elif c == "*":
+            before_deep = glob[i - 1] if i > 0 else None
+            star_count = 1
+            while i + 1 < len(glob) and glob[i + 1] == "*":
+                star_count += 1
+                i += 1
+            after_deep = glob[i + 1] if i + 1 < len(glob) else None
+            is_deep = (
+                star_count > 1
+                and (before_deep == "/" or before_deep is None)
+                and (after_deep == "/" or after_deep is None)
+            )
+            if is_deep:
+                tokens.append("((?:[^/]*(?:/|$))*)")
+                i += 1
+            else:
+                tokens.append("([^/]*)")
+        else:
+            if c == "?":
+                tokens.append(".")
+            elif c == "[":
+                tokens.append("[")
+            elif c == "]":
+                tokens.append("]")
+            elif c == "{":
+                in_group = True
+                tokens.append("(")
+            elif c == "}":
+                in_group = False
+                tokens.append(")")
+            elif c == "," and in_group:
+                tokens.append("|")
+            else:
+                tokens.append("\\" + c if c in escaped_chars else c)
+        i += 1
+
+    tokens.append("$")
+    return re.compile("".join(tokens))
diff --git a/playwright/_impl/_helper.py b/playwright/_impl/_helper.py
index 1b4902613..b68ad6f0b 100644
--- a/playwright/_impl/_helper.py
+++ b/playwright/_impl/_helper.py
@@ -12,7 +12,6 @@
 # See the License for the specific language governing permissions and
 # limitations under the License.
 import asyncio
-import fnmatch
 import inspect
 import math
 import os
@@ -41,6 +40,7 @@
 
 from playwright._impl._api_structures import NameValue
 from playwright._impl._errors import Error, TargetClosedError, TimeoutError
+from playwright._impl._glob import glob_to_regex
 from playwright._impl._str_utils import escape_regex_flags
 
 if sys.version_info >= (3, 8):  # pragma: no cover
@@ -149,7 +149,7 @@ def __init__(self, base_url: Union[str, None], match: URLMatch) -> None:
         if isinstance(match, str):
             if base_url and not match.startswith("*"):
                 match = urljoin(base_url, match)
-            regex = fnmatch.translate(match)
+            regex = glob_to_regex(match)
             self._regex_obj = re.compile(regex)
         elif isinstance(match, Pattern):
             self._regex_obj = match
diff --git a/tests/async/test_browsercontext_request_fallback.py b/tests/async/test_browsercontext_request_fallback.py
index f3959490b..b198a4ebd 100644
--- a/tests/async/test_browsercontext_request_fallback.py
+++ b/tests/async/test_browsercontext_request_fallback.py
@@ -185,10 +185,9 @@ async def handler_with_header_mods(route: Route) -> None:
     await context.route("**/*", handler_with_header_mods)
 
     await page.goto(server.EMPTY_PAGE)
-    async with page.expect_request("/sleep.zzz") as request_info:
+    with server.expect_request("/sleep.zzz") as server_request_info:
         await page.evaluate("() => fetch('/sleep.zzz')")
-    request = await request_info.value
-    values.append(request.headers.get("foo"))
+    values.append(server_request_info.value.getHeader("foo"))
     assert values == ["bar", "bar", "bar"]
 
 
diff --git a/tests/async/test_interception.py b/tests/async/test_interception.py
index 911d7ddd8..01f932360 100644
--- a/tests/async/test_interception.py
+++ b/tests/async/test_interception.py
@@ -20,6 +20,7 @@
 
 import pytest
 
+from playwright._impl._glob import glob_to_regex
 from playwright.async_api import (
     Browser,
     BrowserContext,
@@ -1041,3 +1042,47 @@ async def handle_request(route: Route) -> None:
     assert response
     assert response.status == 200
     assert await response.json() == {"foo": "bar"}
+
+
+async def test_glob_to_regex() -> None:
+    assert glob_to_regex("**/*.js").match("https://localhost:8080/foo.js")
+    assert not glob_to_regex("**/*.css").match("https://localhost:8080/foo.js")
+    assert not glob_to_regex("*.js").match("https://localhost:8080/foo.js")
+    assert glob_to_regex("https://**/*.js").match("https://localhost:8080/foo.js")
+    assert glob_to_regex("http://localhost:8080/simple/path.js").match(
+        "http://localhost:8080/simple/path.js"
+    )
+    assert glob_to_regex("http://localhost:8080/?imple/path.js").match(
+        "http://localhost:8080/Simple/path.js"
+    )
+    assert glob_to_regex("**/{a,b}.js").match("https://localhost:8080/a.js")
+    assert glob_to_regex("**/{a,b}.js").match("https://localhost:8080/b.js")
+    assert not glob_to_regex("**/{a,b}.js").match("https://localhost:8080/c.js")
+
+    assert glob_to_regex("**/*.{png,jpg,jpeg}").match("https://localhost:8080/c.jpg")
+    assert glob_to_regex("**/*.{png,jpg,jpeg}").match("https://localhost:8080/c.jpeg")
+    assert glob_to_regex("**/*.{png,jpg,jpeg}").match("https://localhost:8080/c.png")
+    assert not glob_to_regex("**/*.{png,jpg,jpeg}").match(
+        "https://localhost:8080/c.css"
+    )
+    assert glob_to_regex("foo*").match("foo.js")
+    assert not glob_to_regex("foo*").match("foo/bar.js")
+    assert not glob_to_regex("http://localhost:3000/signin-oidc*").match(
+        "http://localhost:3000/signin-oidc/foo"
+    )
+    assert glob_to_regex("http://localhost:3000/signin-oidc*").match(
+        "http://localhost:3000/signin-oidcnice"
+    )
+
+    assert glob_to_regex("**/three-columns/settings.html?**id=[a-z]**").match(
+        "http://mydomain:8080/blah/blah/three-columns/settings.html?id=settings-e3c58efe-02e9-44b0-97ac-dd138100cf7c&blah"
+    )
+
+    assert glob_to_regex("\\?") == re.compile(r"^\?$")
+    assert glob_to_regex("\\") == re.compile(r"^\\$")
+    assert glob_to_regex("\\\\") == re.compile(r"^\\$")
+    assert glob_to_regex("\\[") == re.compile(r"^\[$")
+    assert glob_to_regex("[a-z]") == re.compile(r"^[a-z]$")
+    assert glob_to_regex("$^+.\\*()|\\?\\{\\}\\[\\]") == re.compile(
+        r"^\$\^\+\.\*\(\)\|\?\{\}\[\]$"
+    )
diff --git a/tests/async/test_page_request_fallback.py b/tests/async/test_page_request_fallback.py
index 456c911a3..1cea1204a 100644
--- a/tests/async/test_page_request_fallback.py
+++ b/tests/async/test_page_request_fallback.py
@@ -164,10 +164,9 @@ async def handler_with_header_mods(route: Route) -> None:
     await page.route("**/*", handler_with_header_mods)
 
     await page.goto(server.EMPTY_PAGE)
-    async with page.expect_request("/sleep.zzz") as request_info:
+    with server.expect_request("/sleep.zzz") as server_request_info:
         await page.evaluate("() => fetch('/sleep.zzz')")
-    request = await request_info.value
-    values.append(request.headers.get("foo"))
+    values.append(server_request_info.value.getHeader("foo"))
     assert values == ["bar", "bar", "bar"]
 
 
diff --git a/tests/sync/test_browsercontext_request_fallback.py b/tests/sync/test_browsercontext_request_fallback.py
index e653800d7..6feb19942 100644
--- a/tests/sync/test_browsercontext_request_fallback.py
+++ b/tests/sync/test_browsercontext_request_fallback.py
@@ -174,10 +174,9 @@ def handler_with_header_mods(route: Route) -> None:
     context.route("**/*", handler_with_header_mods)
 
     page.goto(server.EMPTY_PAGE)
-    with page.expect_request("/sleep.zzz") as request_info:
+    with server.expect_request("/sleep.zzz") as server_request_info:
         page.evaluate("() => fetch('/sleep.zzz')")
-    request = request_info.value
-    values.append(request.headers.get("foo"))
+    values.append(server_request_info.value.getHeader("foo"))
     assert values == ["bar", "bar", "bar"]
 
 
diff --git a/tests/sync/test_page_request_fallback.py b/tests/sync/test_page_request_fallback.py
index 09a3c9845..53570960c 100644
--- a/tests/sync/test_page_request_fallback.py
+++ b/tests/sync/test_page_request_fallback.py
@@ -162,10 +162,9 @@ def handler_with_header_mods(route: Route) -> None:
     page.route("**/*", handler_with_header_mods)
 
     page.goto(server.EMPTY_PAGE)
-    with page.expect_request("/sleep.zzz") as request_info:
+    with server.expect_request("/sleep.zzz") as server_request_info:
         page.evaluate("() => fetch('/sleep.zzz')")
-    request = request_info.value
-    _append_with_return_value(values, request.headers.get("foo"))
+    _append_with_return_value(values, server_request_info.value.getHeader("foo"))
     assert values == ["bar", "bar", "bar"]