diff --git a/playwright/_impl/_glob.py b/playwright/_impl/_glob.py
index 2d899a789..08b7ce466 100644
--- a/playwright/_impl/_glob.py
+++ b/playwright/_impl/_glob.py
@@ -11,13 +11,12 @@
 # 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]":
+def glob_to_regex_pattern(glob: str) -> str:
     tokens = ["^"]
     in_group = False
 
@@ -46,23 +45,20 @@ def glob_to_regex(glob: str) -> "re.Pattern[str]":
             else:
                 tokens.append("([^/]*)")
         else:
-            if c == "?":
-                tokens.append(".")
-            elif c == "[":
-                tokens.append("[")
-            elif c == "]":
-                tokens.append("]")
-            elif c == "{":
+            if c == "{":
                 in_group = True
                 tokens.append("(")
             elif c == "}":
                 in_group = False
                 tokens.append(")")
-            elif c == "," and in_group:
-                tokens.append("|")
+            elif c == ",":
+                if in_group:
+                    tokens.append("|")
+                else:
+                    tokens.append("\\" + c)
             else:
                 tokens.append("\\" + c if c in escaped_chars else c)
         i += 1
 
     tokens.append("$")
-    return re.compile("".join(tokens))
+    return "".join(tokens)
diff --git a/playwright/_impl/_helper.py b/playwright/_impl/_helper.py
index 2f7ab57b0..96acb8857 100644
--- a/playwright/_impl/_helper.py
+++ b/playwright/_impl/_helper.py
@@ -44,7 +44,7 @@
     is_target_closed_error,
     rewrite_error,
 )
-from playwright._impl._glob import glob_to_regex
+from playwright._impl._glob import glob_to_regex_pattern
 from playwright._impl._greenlets import RouteGreenlet
 from playwright._impl._str_utils import escape_regex_flags
 
@@ -144,31 +144,103 @@ class FrameNavigatedEvent(TypedDict):
 
 
 def url_matches(
-    base_url: Optional[str], url_string: str, match: Optional[URLMatch]
+    base_url: Optional[str],
+    url_string: str,
+    match: Optional[URLMatch],
+    websocket_url: bool = None,
 ) -> bool:
     if not match:
         return True
-    if isinstance(match, str) and match[0] != "*":
-        # Allow http(s) baseURL to match ws(s) urls.
-        if (
-            base_url
-            and re.match(r"^https?://", base_url)
-            and re.match(r"^wss?://", url_string)
-        ):
-            base_url = re.sub(r"^http", "ws", base_url)
-        if base_url:
-            match = urljoin(base_url, match)
-        parsed = urlparse(match)
-        if parsed.path == "":
-            parsed = parsed._replace(path="/")
-            match = parsed.geturl()
     if isinstance(match, str):
-        match = glob_to_regex(match)
+        match = re.compile(
+            resolve_glob_to_regex_pattern(base_url, match, websocket_url)
+        )
     if isinstance(match, Pattern):
         return bool(match.search(url_string))
     return match(url_string)
 
 
+def resolve_glob_to_regex_pattern(
+    base_url: Optional[str], glob: str, websocket_url: bool = None
+) -> str:
+    if websocket_url:
+        base_url = to_websocket_base_url(base_url)
+    glob = resolve_glob_base(base_url, glob)
+    return glob_to_regex_pattern(glob)
+
+
+def to_websocket_base_url(base_url: Optional[str]) -> Optional[str]:
+    if base_url is not None and re.match(r"^https?://", base_url):
+        base_url = re.sub(r"^http", "ws", base_url)
+    return base_url
+
+
+def resolve_glob_base(base_url: Optional[str], match: str) -> str:
+    if match[0] == "*":
+        return match
+
+    token_map: Dict[str, str] = {}
+
+    def map_token(original: str, replacement: str) -> str:
+        if len(original) == 0:
+            return ""
+        token_map[replacement] = original
+        return replacement
+
+    # Escaped `\\?` behaves the same as `?` in our glob patterns.
+    match = match.replace(r"\\?", "?")
+    # Glob symbols may be escaped in the URL and some of them such as ? affect resolution,
+    # so we replace them with safe components first.
+    processed_parts = []
+    for index, token in enumerate(match.split("/")):
+        if token in (".", "..", ""):
+            processed_parts.append(token)
+            continue
+        # Handle special case of http*://, note that the new schema has to be
+        # a web schema so that slashes are properly inserted after domain.
+        if index == 0 and token.endswith(":"):
+            # Using a simple replacement for the scheme part
+            processed_parts.append(map_token(token, "http:"))
+            continue
+        question_index = token.find("?")
+        if question_index == -1:
+            processed_parts.append(map_token(token, f"$_{index}_$"))
+        else:
+            new_prefix = map_token(token[:question_index], f"$_{index}_$")
+            new_suffix = map_token(token[question_index:], f"?$_{index}_$")
+            processed_parts.append(new_prefix + new_suffix)
+
+    relative_path = "/".join(processed_parts)
+    resolved_url = urljoin(base_url if base_url is not None else "", relative_path)
+
+    for replacement, original in token_map.items():
+        resolved_url = resolved_url.replace(replacement, original, 1)
+
+    return ensure_trailing_slash(resolved_url)
+
+
+# In Node.js, new URL('http://localhost') returns 'http://localhost/'.
+# To ensure the same url matching behavior, do the same.
+def ensure_trailing_slash(url: str) -> str:
+    split = url.split("://", maxsplit=1)
+    if len(split) == 2:
+        # URL parser doesn't like strange/unknown schemes, so we replace it for parsing, then put it back
+        parsable_url = "http://" + split[1]
+    else:
+        # Given current rules, this should never happen _and_ still be a valid matcher. We require the protocol to be part of the match,
+        # so either the user is using a glob that starts with "*" (and none of this code is running), or the user actually has `something://` in `match`
+        parsable_url = url
+    parsed = urlparse(parsable_url, allow_fragments=True)
+    if len(split) == 2:
+        # Replace the scheme that we removed earlier
+        parsed = parsed._replace(scheme=split[0])
+    if parsed.path == "":
+        parsed = parsed._replace(path="/")
+        url = parsed.geturl()
+
+    return url
+
+
 class HarLookupResult(TypedDict, total=False):
     action: Literal["error", "redirect", "fulfill", "noentry"]
     message: Optional[str]
diff --git a/playwright/_impl/_network.py b/playwright/_impl/_network.py
index 4b15531af..6492c4311 100644
--- a/playwright/_impl/_network.py
+++ b/playwright/_impl/_network.py
@@ -754,7 +754,7 @@ def prepare_interception_patterns(
         return patterns
 
     def matches(self, ws_url: str) -> bool:
-        return url_matches(self._base_url, ws_url, self.url)
+        return url_matches(self._base_url, ws_url, self.url, True)
 
     async def handle(self, websocket_route: "WebSocketRoute") -> None:
         coro_or_future = self.handler(websocket_route)
diff --git a/tests/async/test_page_route.py b/tests/async/test_page_route.py
index 017bdac9a..b04f96145 100644
--- a/tests/async/test_page_route.py
+++ b/tests/async/test_page_route.py
@@ -20,7 +20,8 @@
 
 import pytest
 
-from playwright._impl._glob import glob_to_regex
+from playwright._impl._glob import glob_to_regex_pattern
+from playwright._impl._helper import url_matches
 from playwright.async_api import (
     Browser,
     BrowserContext,
@@ -29,6 +30,7 @@
     Playwright,
     Request,
     Route,
+    expect,
 )
 from tests.server import Server, TestServerRequest
 from tests.utils import must
@@ -1051,17 +1053,19 @@ async def handle_request(route: Route) -> None:
     assert await response.json() == {"foo": "bar"}
 
 
-async def test_glob_to_regex() -> None:
+async def test_should_work_with_glob() -> None:
+    def glob_to_regex(pattern: str) -> re.Pattern:
+        return re.compile(glob_to_regex_pattern(pattern))
+
     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 not glob_to_regex("*.js").match(
+        "https://localhost:8080/foo.js"
+    )  # Doesn"t match path separator
     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")
@@ -1081,15 +1085,119 @@ async def test_glob_to_regex() -> None:
         "http://localhost:3000/signin-oidcnice"
     )
 
-    assert glob_to_regex("**/three-columns/settings.html?**id=[a-z]**").match(
+    # range [] is NOT supported
+    assert glob_to_regex("**/api/v[0-9]").fullmatch("http://example.com/api/v[0-9]")
+    assert not glob_to_regex("**/api/v[0-9]").fullmatch(
+        "http://example.com/api/version"
+    )
+    assert not glob_to_regex("**/api/v[0-9]").fullmatch(
+        "http://example.com/api/v1"
+    )  # Should not match if [] is literal
+
+    # query params
+    assert glob_to_regex("**/api\\?param").match("http://example.com/api?param")
+    assert not glob_to_regex("**/api\\?param").match("http://example.com/api-param")
+
+    assert glob_to_regex("**/three-columns/settings.html\\?**id=settings-**").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"^\$\^\+\.\*\(\)\|\?\{\}\[\]$"
+    assert glob_to_regex("\\?").pattern == r"^\?$"
+    assert glob_to_regex("\\").pattern == r"^\\$"
+    assert glob_to_regex("\\\\").pattern == r"^\\$"
+    assert glob_to_regex("\\[").pattern == r"^\[$"
+    assert glob_to_regex("[a-z]").pattern == r"^\[a-z\]$"
+    assert (
+        glob_to_regex("$^+.\\*()|\\?\\{\\}\\[\\]").pattern
+        == r"^\$\^\+\.\*\(\)\|\?\{\}\[\]$"
+    )
+
+    # --- url_matches tests ---
+    # Basic exact and wildcard matching
+    assert url_matches(None, "http://playwright.dev/", "http://playwright.dev")
+    assert url_matches(None, "http://playwright.dev/?a=b", "http://playwright.dev?a=b")
+    assert url_matches(None, "http://playwright.dev/", "h*://playwright.dev")
+    assert url_matches(
+        None, "http://api.playwright.dev/?x=y", "http://*.playwright.dev?x=y"
+    )
+    assert url_matches(None, "http://playwright.dev/foo/bar", "**/foo/**")
+
+    # Relative path matching with base URL
+    assert url_matches("http://playwright.dev", "http://playwright.dev/?x=y", "?x=y")
+    assert url_matches(
+        "http://playwright.dev/foo/", "http://playwright.dev/foo/bar?x=y", "./bar?x=y"
+    )
+
+    # This is not supported, we treat ? as a query separator.
+    assert not url_matches(
+        None,
+        "http://localhost:8080/Simple/path.js",
+        "http://localhost:8080/?imple/path.js",
+    )
+    assert not url_matches(None, "http://playwright.dev/", "http://playwright.?ev")
+    assert url_matches(None, "http://playwright./?ev", "http://playwright.?ev")
+    assert not url_matches(
+        None, "http://playwright.dev/foo", "http://playwright.dev/f??"
+    )
+    assert url_matches(None, "http://playwright.dev/f??", "http://playwright.dev/f??")
+    assert url_matches(
+        None, "http://playwright.dev/?x=y", r"http://playwright.dev\?x=y"
+    )
+    assert url_matches(
+        None, "http://playwright.dev/?x=y", r"http://playwright.dev/\?x=y"
+    )
+    assert url_matches(
+        "http://playwright.dev/foo", "http://playwright.dev/foo?bar", "?bar"
+    )
+    assert url_matches(
+        "http://playwright.dev/foo", "http://playwright.dev/foo?bar", r"\\?bar"
+    )
+    assert url_matches("http://first.host/", "http://second.host/foo", "**/foo")
+    assert url_matches("http://playwright.dev/", "http://localhost/", "*//localhost/")
+
+    # Added for Python implementation
+    assert url_matches(
+        None,
+        "custom://example.com/foo/bar?id=123",
+        "{custom,another}://example.com/foo/bar?id=123",
+    )
+    assert not url_matches(
+        None, "custom://example.com/foo/bar?id=123", "**example.com/foo/bar?id=123"
     )
+
+
+async def test_should_not_support_question_in_glob_pattern(
+    page: Page, playwright: Playwright, server: Server
+) -> None:
+    server.set_route("/index", lambda req: (req.write(b"index-no-hello"), req.finish()))
+    server.set_route(
+        "/index123hello", lambda req: (req.write(b"index123hello"), req.finish())
+    )
+    server.set_route(
+        "/index?hello", lambda req: (req.write(b"index?hello"), req.finish())
+    )
+    server.set_route(
+        "/index1hello", lambda req: (req.write(b"index1hello"), req.finish())
+    )
+
+    async def handle_any_char(route: Route) -> None:
+        await route.fulfill(body="intercepted any character")
+
+    await page.route("**/index?hello", handle_any_char)
+
+    async def handle_question_mark(route: Route) -> None:
+        await route.fulfill(body="intercepted question mark")
+
+    await page.route(r"**/index\?hello", handle_question_mark)
+
+    await page.goto(server.PREFIX + "/index?hello")
+    await expect(page.locator("body")).to_have_text("intercepted question mark")
+
+    await page.goto(server.PREFIX + "/index")
+    await expect(page.locator("body")).to_have_text("index-no-hello")
+
+    await page.goto(server.PREFIX + "/index1hello")
+    await expect(page.locator("body")).to_have_text("index1hello")
+
+    await page.goto(server.PREFIX + "/index123hello")
+    await expect(page.locator("body")).to_have_text("index123hello")
diff --git a/tests/async/test_request_intercept.py b/tests/async/test_request_intercept.py
index 316e0b102..75746bbca 100644
--- a/tests/async/test_request_intercept.py
+++ b/tests/async/test_request_intercept.py
@@ -175,3 +175,17 @@ async def test_should_give_access_to_the_intercepted_response_body(
         route.fulfill(response=response),
         eval_task,
     )
+
+
+async def test_should_intercept_by_glob(page: Page, server: Server) -> None:
+    await page.goto(server.EMPTY_PAGE)
+    await page.route(
+        "http://localhos**?*oo",
+        lambda route: route.fulfill(body="intercepted", status=200),
+    )
+
+    result = await page.evaluate(
+        "url => fetch(url).then(r => r.text())", server.PREFIX + "/?foo"
+    )
+
+    assert result == "intercepted"
diff --git a/tests/sync/test_request_intercept.py b/tests/sync/test_request_intercept.py
index 8df41c0c2..a54c0ad71 100644
--- a/tests/sync/test_request_intercept.py
+++ b/tests/sync/test_request_intercept.py
@@ -131,3 +131,17 @@ def handle_route(route: Route) -> None:
     assert request.uri.decode() == "/title.html"
     original = (assetdir / "title.html").read_text()
     assert response.text() == original
+
+
+def test_should_intercept_by_glob(page: Page, server: Server) -> None:
+    page.goto(server.EMPTY_PAGE)
+    page.route(
+        "http://localhos**?*oo",
+        lambda route: route.fulfill(body="intercepted", status=200),
+    )
+
+    result = page.evaluate(
+        "url => fetch(url).then(r => r.text())", server.PREFIX + "/?foo"
+    )
+
+    assert result == "intercepted"