diff --git a/doc/source/whatsnew/v3.0.0.rst b/doc/source/whatsnew/v3.0.0.rst
index 10b56011c9640..fbe8164863237 100644
--- a/doc/source/whatsnew/v3.0.0.rst
+++ b/doc/source/whatsnew/v3.0.0.rst
@@ -1117,6 +1117,7 @@ Conversion
 
 Strings
 ^^^^^^^
+- Bug in :meth:`Series.str.match` failing to raise when given a compiled ``re.Pattern`` object and conflicting ``case`` or ``flags`` arguments (:issue:`62240`)
 - Bug in :meth:`Series.str.replace` raising an error on valid group references (``\1``, ``\2``, etc.) on series converted to PyArrow backend dtype (:issue:`62653`)
 - Bug in :meth:`Series.str.zfill` raising ``AttributeError`` for :class:`ArrowDtype` (:issue:`61485`)
 - Bug in :meth:`Series.value_counts` would not respect ``sort=False`` for series having ``string`` dtype (:issue:`55224`)
diff --git a/pandas/core/strings/accessor.py b/pandas/core/strings/accessor.py
index 110473be5d27c..210a177d073f7 100644
--- a/pandas/core/strings/accessor.py
+++ b/pandas/core/strings/accessor.py
@@ -1351,7 +1351,13 @@ def contains(
         return self._wrap_result(result, fill_value=na, returns_string=False)
 
     @forbid_nonstring_types(["bytes"])
-    def match(self, pat: str, case: bool = True, flags: int = 0, na=lib.no_default):
+    def match(
+        self,
+        pat: str | re.Pattern,
+        case: bool | lib.NoDefault = lib.no_default,
+        flags: int | lib.NoDefault = lib.no_default,
+        na=lib.no_default,
+    ):
         """
         Determine if each string starts with a match of a regular expression.
 
@@ -1397,6 +1403,39 @@ def match(self, pat: str, case: bool = True, flags: int = 0, na=lib.no_default):
         2   False
         dtype: bool
         """
+        if flags is not lib.no_default:
+            # pat.flags will have re.U regardless, so we need to add it here
+            # before checking for a match
+            flags = flags | re.U
+            if is_re(pat):
+                if pat.flags != flags:
+                    raise ValueError(
+                        "Cannot both specify 'flags' and pass a compiled regexp "
+                        "object with conflicting flags"
+                    )
+            else:
+                pat = re.compile(pat, flags=flags)
+            # set flags=0 to ensure that when we call
+            #  re.compile(pat, flags=flags) the constructor does not raise.
+            flags = 0
+        else:
+            flags = 0
+
+        if case is lib.no_default:
+            if is_re(pat):
+                case = not bool(pat.flags & re.IGNORECASE)
+            else:
+                # Case-sensitive default
+                case = True
+        elif is_re(pat):
+            implicit_case = not bool(pat.flags & re.IGNORECASE)
+            if implicit_case != case:
+                # GH#62240
+                raise ValueError(
+                    "Cannot both specify 'case' and pass a compiled regexp "
+                    "object with conflicting case-sensitivity"
+                )
+
         result = self._data.array._str_match(pat, case=case, flags=flags, na=na)
         return self._wrap_result(result, fill_value=na, returns_string=False)
 
diff --git a/pandas/core/strings/object_array.py b/pandas/core/strings/object_array.py
index c948fec8e7aa2..bd8fb2e2326f6 100644
--- a/pandas/core/strings/object_array.py
+++ b/pandas/core/strings/object_array.py
@@ -238,7 +238,17 @@ def _str_match(
         if not case:
             flags |= re.IGNORECASE
 
-        regex = re.compile(pat, flags=flags)
+        if isinstance(pat, re.Pattern):
+            # We need to check that flags matches pat.flags.
+            # pat.flags will have re.U regardless, so we need to add it here
+            # before checking for a match
+            flags = flags | re.U
+
+            if flags != pat.flags:
+                raise ValueError("Cannot pass flags that do not match pat.flags")
+            regex = pat
+        else:
+            regex = re.compile(pat, flags=flags)
 
         f = lambda x: regex.match(x) is not None
         return self._str_map(f, na_value=na, dtype=np.dtype(bool))
diff --git a/pandas/tests/strings/test_find_replace.py b/pandas/tests/strings/test_find_replace.py
index 12a3bd63cea90..2a244f8329345 100644
--- a/pandas/tests/strings/test_find_replace.py
+++ b/pandas/tests/strings/test_find_replace.py
@@ -1004,26 +1004,27 @@ def test_match_compiled_regex(any_string_dtype):
     expected = Series([True, False, True, False], dtype=expected_dtype)
     tm.assert_series_equal(result, expected)
 
-    # TODO this currently works for pyarrow-backed dtypes but raises for python
-    if any_string_dtype == "string" and any_string_dtype.storage == "pyarrow":
-        result = values.str.match(re.compile("ab"), case=False)
-        expected = Series([True, True, True, True], dtype=expected_dtype)
-        tm.assert_series_equal(result, expected)
-    else:
-        with pytest.raises(
-            ValueError, match="cannot process flags argument with a compiled pattern"
-        ):
-            values.str.match(re.compile("ab"), case=False)
+    msg = (
+        "Cannot both specify 'case' and pass a compiled "
+        "regexp object with conflicting case-sensitivity"
+    )
+    with pytest.raises(ValueError, match=msg):
+        values.str.match(re.compile("ab"), case=False)
 
     result = values.str.match(re.compile("ab", flags=re.IGNORECASE))
     expected = Series([True, True, True, True], dtype=expected_dtype)
     tm.assert_series_equal(result, expected)
 
-    with pytest.raises(
-        ValueError, match="cannot process flags argument with a compiled pattern"
-    ):
+    msg = (
+        "Cannot both specify 'flags' and pass a compiled "
+        "regexp object with conflicting flags"
+    )
+    with pytest.raises(ValueError, match=msg):
         values.str.match(re.compile("ab"), flags=re.IGNORECASE)
 
+    # But if the flags match you're OK
+    values.str.match(re.compile("ab", flags=re.IGNORECASE), flags=re.IGNORECASE)
+
 
 @pytest.mark.parametrize(
     "pat, case, exp",