diff --git a/pandas/core/arrays/datetimelike.py b/pandas/core/arrays/datetimelike.py
index a25a698856747..822a9a94bbbd9 100644
--- a/pandas/core/arrays/datetimelike.py
+++ b/pandas/core/arrays/datetimelike.py
@@ -1488,7 +1488,13 @@ def __rsub__(self, other):
             return (-self) + other
 
         # We get here with e.g. datetime objects
-        return -(self - other)
+        datetime_result = self - other
+        if isinstance(datetime_result, DatetimeArray):
+            raise TypeError(
+                "TypeError: unsupported operand type(s) for -: "
+                f"'{type(self).__name__}' and '{type(other).__name__}'"
+            )
+        return -(datetime_result)
 
     def __iadd__(self, other) -> Self:
         result = self + other
diff --git a/pandas/tests/arithmetic/test_datetime64.py b/pandas/tests/arithmetic/test_datetime64.py
index 26dfcf088e74b..c4d189a13f25a 100644
--- a/pandas/tests/arithmetic/test_datetime64.py
+++ b/pandas/tests/arithmetic/test_datetime64.py
@@ -15,6 +15,7 @@
 
 import numpy as np
 import pytest
+import re
 
 from pandas._libs.tslibs.conversion import localize_pydatetime
 from pandas._libs.tslibs.offsets import shift_months
@@ -1273,8 +1274,10 @@ def test_dt64arr_series_sub_tick_DateOffset(self, box_with_array):
 
         result2 = -pd.offsets.Second(5) + ser
         tm.assert_equal(result2, expected)
-        msg = "(bad|unsupported) operand type for unary"
-        with pytest.raises(TypeError, match=msg):
+        msg = (
+            "TypeError: unsupported operand type(s) for -: 'DatetimeArray' and 'Second'"
+        )
+        with pytest.raises(TypeError, match=re.escape(msg)):
             pd.offsets.Second(5) - ser
 
     @pytest.mark.parametrize(
@@ -1318,10 +1321,8 @@ def test_dti_add_tick_tzaware(self, tz_aware_fixture, box_with_array):
             roundtrip = offset - scalar
             tm.assert_equal(roundtrip, dates)
 
-            msg = "|".join(
-                ["bad operand type for unary -", "cannot subtract DatetimeArray"]
-            )
-            with pytest.raises(TypeError, match=msg):
+            msg = f"TypeError: unsupported operand type(s) for -: 'DatetimeArray' and '{type(scalar).__name__}'"
+            with pytest.raises(TypeError, match=re.escape(msg)):
                 scalar - dates
 
     # -------------------------------------------------------------