diff --git a/stdlib/3/pathlib.pyi b/stdlib/3/pathlib.pyi
index 259bafef7..b76f2ec5b 100644
--- a/stdlib/3/pathlib.pyi
+++ b/stdlib/3/pathlib.pyi
@@ -45,12 +45,16 @@ class PurePath(_PurePathBase):
     def as_uri(self) -> str: ...
     def is_absolute(self) -> bool: ...
     def is_reserved(self) -> bool: ...
+    if sys.version_info >= (3, 9):
+        def is_relative_to(self, *other: Union[str, os.PathLike[str]]) -> bool: ...
     def match(self, path_pattern: str) -> bool: ...
     if sys.version_info < (3, 6):
         def relative_to(self: _P, *other: Union[str, PurePath]) -> _P: ...
     else:
         def relative_to(self: _P, *other: Union[str, os.PathLike[str]]) -> _P: ...
     def with_name(self: _P, name: str) -> _P: ...
+    if sys.version_info >= (3, 9):
+        def with_stem(self: _P, stem: str) -> _P: ...
     def with_suffix(self: _P, suffix: str) -> _P: ...
     if sys.version_info < (3, 6):
         def joinpath(self: _P, *other: Union[str, PurePath]) -> _P: ...
@@ -105,6 +109,8 @@ class Path(PurePath):
     def open(self, mode: str, buffering: int = ..., encoding: Optional[str] = ..., errors: Optional[str] = ...,
              newline: Optional[str] = ...) -> IO[Any]: ...
     def owner(self) -> str: ...
+    if sys.version_info >= (3, 9):
+        def readlink(self: _P) -> _P: ...
     if sys.version_info >= (3, 8):
         def rename(self: _P, target: Union[str, PurePath]) -> _P: ...
         def replace(self: _P, target: Union[str, PurePath]) -> _P: ...
diff --git a/third_party/2/pathlib2.pyi b/third_party/2/pathlib2.pyi
index 259bafef7..b76f2ec5b 100644
--- a/third_party/2/pathlib2.pyi
+++ b/third_party/2/pathlib2.pyi
@@ -45,12 +45,16 @@ class PurePath(_PurePathBase):
     def as_uri(self) -> str: ...
     def is_absolute(self) -> bool: ...
     def is_reserved(self) -> bool: ...
+    if sys.version_info >= (3, 9):
+        def is_relative_to(self, *other: Union[str, os.PathLike[str]]) -> bool: ...
     def match(self, path_pattern: str) -> bool: ...
     if sys.version_info < (3, 6):
         def relative_to(self: _P, *other: Union[str, PurePath]) -> _P: ...
     else:
         def relative_to(self: _P, *other: Union[str, os.PathLike[str]]) -> _P: ...
     def with_name(self: _P, name: str) -> _P: ...
+    if sys.version_info >= (3, 9):
+        def with_stem(self: _P, stem: str) -> _P: ...
     def with_suffix(self: _P, suffix: str) -> _P: ...
     if sys.version_info < (3, 6):
         def joinpath(self: _P, *other: Union[str, PurePath]) -> _P: ...
@@ -105,6 +109,8 @@ class Path(PurePath):
     def open(self, mode: str, buffering: int = ..., encoding: Optional[str] = ..., errors: Optional[str] = ...,
              newline: Optional[str] = ...) -> IO[Any]: ...
     def owner(self) -> str: ...
+    if sys.version_info >= (3, 9):
+        def readlink(self: _P) -> _P: ...
     if sys.version_info >= (3, 8):
         def rename(self: _P, target: Union[str, PurePath]) -> _P: ...
         def replace(self: _P, target: Union[str, PurePath]) -> _P: ...