diff --git a/stdlib/datetime.pyi b/stdlib/datetime.pyi
index dc651cb3b..e612fcd4c 100644
--- a/stdlib/datetime.pyi
+++ b/stdlib/datetime.pyi
@@ -1,9 +1,10 @@
 import sys
 from time import struct_time
-from typing import ClassVar, NamedTuple, SupportsAbs, Type, TypeVar, overload
+from typing import ClassVar, NamedTuple, NoReturn, SupportsAbs, Type, TypeVar, overload
 from typing_extensions import final
 
 _S = TypeVar("_S")
+_D = TypeVar("_D", bound=date)
 
 MINYEAR: int
 MAXYEAR: int
@@ -68,13 +69,22 @@ class date:
     if sys.version_info >= (3, 8):
         def __add__(self: _S, other: timedelta) -> _S: ...
         def __radd__(self: _S, other: timedelta) -> _S: ...
+        @overload
+        def __sub__(self: _D, other: timedelta) -> _D: ...
+        @overload
+        def __sub__(self, other: datetime) -> NoReturn: ...
+        @overload
+        def __sub__(self: _D, other: _D) -> timedelta: ...
     else:
+        # Prior to Python 3.8, arithmetic operations always returned `date`, even in subclasses
         def __add__(self, other: timedelta) -> date: ...
         def __radd__(self, other: timedelta) -> date: ...
-    @overload
-    def __sub__(self, other: timedelta) -> date: ...
-    @overload
-    def __sub__(self, other: date) -> timedelta: ...
+        @overload
+        def __sub__(self, other: timedelta) -> date: ...
+        @overload
+        def __sub__(self, other: datetime) -> NoReturn: ...
+        @overload
+        def __sub__(self, other: date) -> timedelta: ...
     def __hash__(self) -> int: ...
     def weekday(self) -> int: ...
     def isoweekday(self) -> int: ...
@@ -267,13 +277,19 @@ class datetime(date):
     def __lt__(self, other: datetime) -> bool: ...  # type: ignore
     def __ge__(self, other: datetime) -> bool: ...  # type: ignore
     def __gt__(self, other: datetime) -> bool: ...  # type: ignore
-    if sys.version_info < (3, 8):
+    if sys.version_info >= (3, 8):
+        @overload  # type: ignore[override]
+        def __sub__(self: _D, other: timedelta) -> _D: ...
+        @overload
+        def __sub__(self: _D, other: _D) -> timedelta: ...
+    else:
+        # Prior to Python 3.8, arithmetic operations always returned `datetime`, even in subclasses
         def __add__(self, other: timedelta) -> datetime: ...
         def __radd__(self, other: timedelta) -> datetime: ...
-    @overload  # type: ignore
-    def __sub__(self, other: datetime) -> timedelta: ...
-    @overload
-    def __sub__(self, other: timedelta) -> datetime: ...
+        @overload  # type: ignore[override]
+        def __sub__(self, other: datetime) -> timedelta: ...
+        @overload
+        def __sub__(self, other: timedelta) -> datetime: ...
     if sys.version_info >= (3, 9):
         def isocalendar(self) -> _IsoCalendarDate: ...
     else: