diff --git a/pandas-stubs/core/series.pyi b/pandas-stubs/core/series.pyi
index 0249bb5c8..e451c8efc 100644
--- a/pandas-stubs/core/series.pyi
+++ b/pandas-stubs/core/series.pyi
@@ -1,5 +1,6 @@
 from datetime import (
     date,
+    datetime,
     time,
 )
 from typing import (
@@ -1218,7 +1219,9 @@ class Series(IndexOpsMixin, NDFrame, Generic[S1]):
     def __rtruediv__(self, other: num | _ListLike | Series[S1]) -> Series: ...
     def __rxor__(self, other: num | _ListLike | Series[S1]) -> Series[_bool]: ...
     @overload
-    def __sub__(self, other: Timestamp | TimestampSeries) -> TimedeltaSeries: ...
+    def __sub__(
+        self, other: Timestamp | datetime | TimestampSeries
+    ) -> TimedeltaSeries: ...
     @overload
     def __sub__(
         self, other: Timedelta | TimedeltaSeries | TimedeltaIndex
diff --git a/tests/test_timefuncs.py b/tests/test_timefuncs.py
index 8e5a39fea..ff9d86bc1 100644
--- a/tests/test_timefuncs.py
+++ b/tests/test_timefuncs.py
@@ -120,8 +120,6 @@ def test_timedelta_series_arithmetic() -> None:
 
 
 def test_timestamp_timedelta_series_arithmetic() -> None:
-    ts = pd.Timestamp("2022-03-05")
-    s1 = pd.Series(["2022-03-05", "2022-03-06"])
     ts1 = pd.to_datetime(pd.Series(["2022-03-05", "2022-03-06"]))
     assert isinstance(ts1.iloc[0], pd.Timestamp)
     td1 = pd.to_timedelta([2, 3], "seconds")
@@ -141,6 +139,13 @@ def test_timestamp_timedelta_series_arithmetic() -> None:
     r6 = r1 * 4
     check(assert_type(r6, "TimedeltaSeries"), pd.Series, pd.Timedelta)
 
+    tsp1 = pd.Timestamp("2022-03-05")
+    dt1 = dt.datetime(2022, 9, 1, 12, 5, 30)
+    r7 = ts1 - tsp1
+    check(assert_type(r7, "TimedeltaSeries"), pd.Series, pd.Timedelta)
+    r8 = ts1 - dt1
+    check(assert_type(r8, "TimedeltaSeries"), pd.Series, pd.Timedelta)
+
 
 def test_timestamp_dateoffset_arithmetic() -> None:
     ts = pd.Timestamp("2022-03-18")