diff --git a/AUTHORS b/AUTHORS
index c33cf5fafbd..d6d2737a4bf 100644
--- a/AUTHORS
+++ b/AUTHORS
@@ -180,6 +180,7 @@ Fraser Stark
 Freya Bruhin
 Gabriel Landau
 Gabriel Reis
+Garion Milazzo
 Garvit Shubham
 Gene Wood
 George Kussumoto
diff --git a/changelog/14389.bugfix.rst b/changelog/14389.bugfix.rst
new file mode 100644
index 00000000000..15bccc5bbce
--- /dev/null
+++ b/changelog/14389.bugfix.rst
@@ -0,0 +1 @@
+Improved ``pytest.raises(..., match=...)`` failures to report the mismatched exception as the direct cause of the resulting ``AssertionError``.
diff --git a/src/_pytest/raises.py b/src/_pytest/raises.py
index 82fe2c41c96..d24eddb014a 100644
--- a/src/_pytest/raises.py
+++ b/src/_pytest/raises.py
@@ -698,7 +698,7 @@ def __exit__(
         if not self.matches(exc_val):
             if self._just_propagate:
                 return False
-            raise AssertionError(self._fail_reason)
+            raise AssertionError(self._fail_reason) from exc_val
 
         # Cast to narrow the exception type now that it's verified....
         # even though the TypeGuard in self.matches should be narrowing
diff --git a/testing/python/raises.py b/testing/python/raises.py
index f74d747c0df..70234ddcfb6 100644
--- a/testing/python/raises.py
+++ b/testing/python/raises.py
@@ -179,6 +179,29 @@ def test_invalid_regex():
         result.stdout.no_fnmatch_line("*File*")
         result.stdout.no_fnmatch_line("*line*")
 
+    def test_raises_match_failure_uses_direct_cause(self, pytester: Pytester) -> None:
+        pytester.makepyfile(
+            """
+            import pytest
+
+            def test_raises_match_failure():
+                with pytest.raises(ValueError, match="expected"):
+                    raise ValueError("actual")
+            """
+        )
+        result = pytester.runpytest("--tb=short")
+        assert result.ret == 1
+        result.stdout.fnmatch_lines(
+            [
+                "*ValueError: actual",
+                "*The above exception was the direct cause of the following exception:*",
+                "*E*AssertionError: Regex pattern did not match.*",
+            ]
+        )
+        result.stdout.no_fnmatch_line(
+            "*During handling of the above exception, another exception occurred:*"
+        )
+
     def test_noclass(self) -> None:
         with pytest.raises(TypeError):
             with pytest.raises("wrong"):  # type: ignore[call-overload]