@@ -28,6 +28,7 @@
     Union,
     cast,
 )
+from urllib.parse import urlparse, urlunparse
 from zipfile import ZipFile
 
 import pytest
@@ -1375,3 +1376,19 @@ def __call__(
 
 
 CertFactory = Callable[[], str]
+
+# versions containing fix/backport from https://github.com/python/cpython/pull/113563
+# which changed the behavior of `urllib.parse.urlun{parse,split}`
+url = "////path/to/file"
+has_new_urlun_behavior = url == urlunparse(urlparse(url))
+
+# the above change seems to only impact tests on Windows, so just add skips for that
+skip_needs_new_urlun_behavior_win = pytest.mark.skipif(
+    sys.platform != "win32" or not has_new_urlun_behavior,
+    reason="testing windows behavior for newer CPython",
+)
+
+skip_needs_old_urlun_behavior_win = pytest.mark.skipif(
+    sys.platform != "win32" or has_new_urlun_behavior,
+    reason="testing windows behavior for older CPython",
+)
@@ -35,7 +35,12 @@
     _ensure_quoted_url,
 )
 from pip._internal.network.session import PipSession
-from tests.lib import TestData, make_test_link_collector
+from tests.lib import (
+    TestData,
+    make_test_link_collector,
+    skip_needs_new_urlun_behavior_win,
+    skip_needs_old_urlun_behavior_win,
+)
 
 ACCEPT = ", ".join(
     [
@@ -383,10 +388,12 @@ def test_clean_url_path_with_local_path(path: str, expected: str) -> None:
         pytest.param(
             "file:///T:/path/with spaces/",
             "file:///T:/path/with%20spaces",
-            marks=pytest.mark.skipif(
-                "sys.platform != 'win32' or "
-                "sys.version_info == (3, 13, 0, 'beta', 2)"
-            ),
+            marks=skip_needs_old_urlun_behavior_win,
+        ),
+        pytest.param(
+            "file:///T:/path/with spaces/",
+            "file://///T:/path/with%20spaces",
+            marks=skip_needs_new_urlun_behavior_win,
         ),
         # URL with Windows drive letter, running on non-windows
         # platform. The `:` after the drive should be quoted.
@@ -399,10 +406,12 @@ def test_clean_url_path_with_local_path(path: str, expected: str) -> None:
         pytest.param(
             "git+file:///T:/with space/repo.git@1.0#egg=my-package-1.0",
             "git+file:///T:/with%20space/repo.git@1.0#egg=my-package-1.0",
-            marks=pytest.mark.skipif(
-                "sys.platform != 'win32' or "
-                "sys.version_info == (3, 13, 0, 'beta', 2)"
-            ),
+            marks=skip_needs_old_urlun_behavior_win,
+        ),
+        pytest.param(
+            "git+file:///T:/with space/repo.git@1.0#egg=my-package-1.0",
+            "git+file://///T:/with%20space/repo.git@1.0#egg=my-package-1.0",
+            marks=skip_needs_new_urlun_behavior_win,
         ),
         # Test a VCS URL with a Windows drive letter and revision,
         # running on non-windows platform.
 
@@ -5,6 +5,10 @@
 import pytest
 
 from pip._internal.utils.urls import path_to_url, url_to_path
+from tests.lib import (
+    skip_needs_new_urlun_behavior_win,
+    skip_needs_old_urlun_behavior_win,
+)
 
 
 @pytest.mark.skipif("sys.platform == 'win32'")
@@ -23,12 +27,14 @@ def test_path_to_url_unix() -> None:
         pytest.param(
             r"\\unc\as\path",
             "file://unc/as/path",
-            marks=pytest.mark.skipif(
-                "sys.platform != 'win32' or "
-                "sys.version_info == (3, 13, 0, 'beta', 2)"
-            ),
+            marks=skip_needs_old_urlun_behavior_win,
             id="unc-path",
         ),
+        pytest.param(
+            r"\\unc\as\path",
+            "file:////unc/as/path",
+            marks=skip_needs_new_urlun_behavior_win,
+        ),
     ],
 )
 def test_path_to_url_win(path: str, url: str) -> None: