diff --git a/pandas-stubs/core/indexes/base.pyi b/pandas-stubs/core/indexes/base.pyi
index b8dc94448..297e94057 100644
--- a/pandas-stubs/core/indexes/base.pyi
+++ b/pandas-stubs/core/indexes/base.pyi
@@ -260,7 +260,7 @@ class Index(IndexOpsMixin[S1]):
         **kwargs,
     ) -> Self: ...
     @property
-    def str(self) -> StringMethods[Self, MultiIndex]: ...
+    def str(self) -> StringMethods[Self, MultiIndex, np_ndarray_bool]: ...
     def is_(self, other) -> bool: ...
     def __len__(self) -> int: ...
     def __array__(self, dtype=...) -> np.ndarray: ...
diff --git a/pandas-stubs/core/series.pyi b/pandas-stubs/core/series.pyi
index 209237746..e12fa2cc7 100644
--- a/pandas-stubs/core/series.pyi
+++ b/pandas-stubs/core/series.pyi
@@ -1163,7 +1163,7 @@ class Series(IndexOpsMixin[S1], NDFrame):
     ) -> Series[S1]: ...
     def to_period(self, freq: _str | None = ..., copy: _bool = ...) -> DataFrame: ...
     @property
-    def str(self) -> StringMethods[Series, DataFrame]: ...
+    def str(self) -> StringMethods[Series, DataFrame, Series[bool]]: ...
     @property
     def dt(self) -> CombinedDatetimelikeProperties: ...
     @property
diff --git a/pandas-stubs/core/strings.pyi b/pandas-stubs/core/strings.pyi
index a21074dad..a3596aa5c 100644
--- a/pandas-stubs/core/strings.pyi
+++ b/pandas-stubs/core/strings.pyi
@@ -23,12 +23,15 @@ from pandas.core.base import NoNewAttributesMixin
 from pandas._typing import (
     JoinHow,
     T,
+    np_ndarray_bool,
 )
 
 # The _TS type is what is used for the result of str.split with expand=True
 _TS = TypeVar("_TS", DataFrame, MultiIndex)
+# The _TM type is what is used for the result of str.match
+_TM = TypeVar("_TM", Series[bool], np_ndarray_bool)
 
-class StringMethods(NoNewAttributesMixin, Generic[T, _TS]):
+class StringMethods(NoNewAttributesMixin, Generic[T, _TS, _TM]):
     def __init__(self, data: T) -> None: ...
     def __getitem__(self, key: slice | int) -> T: ...
     def __iter__(self) -> T: ...
@@ -100,7 +103,7 @@ class StringMethods(NoNewAttributesMixin, Generic[T, _TS]):
     ) -> Series[bool]: ...
     def match(
         self, pat: str, case: bool = ..., flags: int = ..., na: Any = ...
-    ) -> T: ...
+    ) -> _TM: ...
     def replace(
         self,
         pat: str,
diff --git a/tests/test_indexes.py b/tests/test_indexes.py
index 85edc3b57..6777736d9 100644
--- a/tests/test_indexes.py
+++ b/tests/test_indexes.py
@@ -113,6 +113,13 @@ def test_str_split() -> None:
     check(assert_type(ind.str.split("-", expand=True), pd.MultiIndex), pd.MultiIndex)
 
 
+def test_str_match() -> None:
+    i = pd.Index(
+        ["applep", "bananap", "Cherryp", "DATEp", "eGGpLANTp", "123p", "23.45p"]
+    )
+    check(assert_type(i.str.match("pp"), npt.NDArray[np.bool_]), np.ndarray, np.bool_)
+
+
 def test_index_rename() -> None:
     ind = pd.Index([1, 2, 3], name="foo")
     ind2 = ind.rename("goo")
diff --git a/tests/test_series.py b/tests/test_series.py
index e68028cc4..bcac374ed 100644
--- a/tests/test_series.py
+++ b/tests/test_series.py
@@ -1481,7 +1481,7 @@ def test_string_accessors():
     check(assert_type(s.str.ljust(80), pd.Series), pd.Series)
     check(assert_type(s.str.lower(), pd.Series), pd.Series)
     check(assert_type(s.str.lstrip("a"), pd.Series), pd.Series)
-    check(assert_type(s.str.match("pp"), pd.Series), pd.Series)
+    check(assert_type(s.str.match("pp"), "pd.Series[bool]"), pd.Series, np.bool_)
     check(assert_type(s.str.normalize("NFD"), pd.Series), pd.Series)
     check(assert_type(s.str.pad(80, "right"), pd.Series), pd.Series)
     check(assert_type(s.str.partition("p"), pd.DataFrame), pd.DataFrame)