diff --git a/Lib/test/test_site.py b/Lib/test/test_site.py
index e66a2db7e9b3c4..6822579ad2a50d 100644
--- a/Lib/test/test_site.py
+++ b/Lib/test/test_site.py
@@ -205,7 +205,7 @@ def test_get_path(self):
             scheme = 'osx_framework_user'
         else:
             scheme = os.name + '_user'
-        self.assertEqual(site._get_path(site._getuserbase()),
+        self.assertEqual(os.path.normpath(site._get_path(site._getuserbase())),
                          sysconfig.get_path('purelib', scheme))
 
     @unittest.skipUnless(site.ENABLE_USER_SITE, "requires access to PEP 370 "
@@ -213,7 +213,7 @@ def test_get_path(self):
     @support.requires_subprocess()
     def test_s_option(self):
         # (ncoghlan) Change this to use script_helper...
-        usersite = site.USER_SITE
+        usersite = os.path.normpath(site.USER_SITE)
         self.assertIn(usersite, sys.path)
 
         env = os.environ.copy()
diff --git a/Lib/test/test_sysconfig.py b/Lib/test/test_sysconfig.py
index c00d7d5b5024f4..27722fbe11ee17 100644
--- a/Lib/test/test_sysconfig.py
+++ b/Lib/test/test_sysconfig.py
@@ -369,7 +369,7 @@ def test_user_similar(self):
                 base = base.replace(sys.base_prefix, sys.prefix)
             if HAS_USER_BASE:
                 user_path = get_path(name, 'posix_user')
-                expected = global_path.replace(base, user, 1)
+                expected = os.path.normpath(global_path.replace(base, user, 1))
                 # bpo-44860: platlib of posix_user doesn't use sys.platlibdir,
                 # whereas posix_prefix does.
                 if name == 'platlib':