diff --git a/pandas/tests/groupby/test_categorical.py b/pandas/tests/groupby/test_categorical.py
index 756de3edd33dd..b5c2de267869d 100644
--- a/pandas/tests/groupby/test_categorical.py
+++ b/pandas/tests/groupby/test_categorical.py
@@ -4,6 +4,8 @@
 import numpy as np
 import pytest
 
+from pandas.compat import PY37, is_platform_windows
+
 import pandas as pd
 from pandas import (
     Categorical,
@@ -208,6 +210,9 @@ def test_level_get_group(observed):
 
 
 # GH#21636 previously flaky on py37
+@pytest.mark.xfail(
+    is_platform_windows() and PY37, reason="Flaky, GH-27902", strict=False
+)
 @pytest.mark.parametrize("ordered", [True, False])
 def test_apply(ordered):
     # GH 10138