diff --git a/dvc/utils/__init__.py b/dvc/utils/__init__.py
index b91a01144..522037f26 100644
--- a/dvc/utils/__init__.py
+++ b/dvc/utils/__init__.py
@@ -319,10 +319,19 @@ def relpath(path, start=os.curdir):
     start = os.path.abspath(os.fspath(start))
 
     # Windows path on different drive than curdir doesn't have relpath
-    if os.name == "nt" and not os.path.commonprefix(
-        [start, os.path.abspath(path)]
-    ):
-        return path
+    if os.name == "nt":
+        # Since python 3.8 os.realpath resolves network shares to their UNC
+        # path. So, to be certain that relative paths correctly captured,
+        # we need to resolve to UNC path first. We resolve only the drive
+        # name so that we don't follow any 'real' symlinks on the path
+        def resolve_network_drive_windows(path_to_resolve):
+            drive, tail = os.path.splitdrive(path_to_resolve)
+            return os.path.join(os.path.realpath(drive), tail)
+
+        path = resolve_network_drive_windows(os.path.abspath(path))
+        start = resolve_network_drive_windows(start)
+        if not os.path.commonprefix([start, path]):
+            return path
     return os.path.relpath(path, start)
 
 
diff --git a/tests/unit/utils/test_utils.py b/tests/unit/utils/test_utils.py
index b86c9044d..43d9c5ba3 100644
--- a/tests/unit/utils/test_utils.py
+++ b/tests/unit/utils/test_utils.py
@@ -113,6 +113,27 @@ def test_relpath():
     assert relpath(path) == relpath(path_info)
 
 
+@pytest.mark.skipif(os.name != "nt", reason="Windows specific")
+def test_relpath_windows(monkeypatch):
+    """test that relpath correctly generated when run on a
+    windows network share. The drive mapped path is mapped
+    to a UNC path by os.path.realpath"""
+
+    def dummy_realpath(path):
+        return path.replace("x:", "\\\\server\\share")
+
+    monkeypatch.setattr(os.path, "realpath", dummy_realpath)
+    assert (
+        relpath("x:\\dir1\\dir2\\file.txt", "\\\\server\\share\\dir1")
+        == "dir2\\file.txt"
+    )
+
+    assert (
+        relpath("y:\\dir1\\dir2\\file.txt", "\\\\server\\share\\dir1")
+        == "y:\\dir1\\dir2\\file.txt"
+    )
+
+
 @pytest.mark.parametrize(
     "inp,out,is_dir,expected",
     [