diff --git a/git/config.py b/git/config.py
index 769929441..c6eaf8f7b 100644
--- a/git/config.py
+++ b/git/config.py
@@ -549,11 +549,21 @@ def _included_paths(self) -> List[Tuple[str, str]]:
         :return:
             The list of paths, where each path is a tuple of (option, value).
         """
+
+        def _all_items(section: str) -> List[Tuple[str, str]]:
+            """Return all (key, value) pairs for a section, including duplicate keys."""
+            return [
+                (key, value)
+                for key, values in self._sections[section].items_all()
+                if key != "__name__"
+                for value in values
+            ]
+
         paths = []
 
         for section in self.sections():
             if section == "include":
-                paths += self.items(section)
+                paths += _all_items(section)
 
             match = CONDITIONAL_INCLUDE_REGEXP.search(section)
             if match is None or self._repo is None:
@@ -579,7 +589,7 @@ def _included_paths(self) -> List[Tuple[str, str]]:
                     )
                 if self._repo.git_dir:
                     if fnmatch.fnmatchcase(os.fspath(self._repo.git_dir), value):
-                        paths += self.items(section)
+                        paths += _all_items(section)
 
             elif keyword == "onbranch":
                 try:
@@ -589,11 +599,11 @@ def _included_paths(self) -> List[Tuple[str, str]]:
                     continue
 
                 if fnmatch.fnmatchcase(branch_name, value):
-                    paths += self.items(section)
+                    paths += _all_items(section)
             elif keyword == "hasconfig:remote.*.url":
                 for remote in self._repo.remotes:
                     if fnmatch.fnmatchcase(remote.url, value):
-                        paths += self.items(section)
+                        paths += _all_items(section)
                         break
         return paths
 
diff --git a/test/test_config.py b/test/test_config.py
index 56ac0f304..11ea52d16 100644
--- a/test/test_config.py
+++ b/test/test_config.py
@@ -246,6 +246,43 @@ def check_test_value(cr, value):
         with GitConfigParser(fpa, read_only=True) as cr:
             check_test_value(cr, tv)
 
+    @with_rw_directory
+    def test_multiple_include_paths_with_same_key(self, rw_dir):
+        """Test that multiple 'path' entries under [include] are all respected.
+
+        Regression test for https://github.com/gitpython-developers/GitPython/issues/2099.
+        Git config allows multiple ``path`` values under ``[include]``, e.g.::
+
+            [include]
+                path = file1
+                path = file2
+
+        Previously only one of these was included because _OMD.items() returns
+        only the last value for each key.
+        """
+        # Create two config files to be included.
+        fp_inc1 = osp.join(rw_dir, "inc1.cfg")
+        fp_inc2 = osp.join(rw_dir, "inc2.cfg")
+        fp_main = osp.join(rw_dir, "main.cfg")
+
+        with GitConfigParser(fp_inc1, read_only=False) as cw:
+            cw.set_value("user", "name", "from-inc1")
+
+        with GitConfigParser(fp_inc2, read_only=False) as cw:
+            cw.set_value("core", "bar", "from-inc2")
+
+        # Write a config with two path entries under a single [include] section.
+        # We write it manually because set_value would overwrite the key.
+        with open(fp_main, "w") as f:
+            f.write("[include]\n")
+            f.write(f"\tpath = {fp_inc1}\n")
+            f.write(f"\tpath = {fp_inc2}\n")
+
+        with GitConfigParser(fp_main, read_only=True) as cr:
+            # Both included files should be loaded.
+            assert cr.get_value("user", "name") == "from-inc1"
+            assert cr.get_value("core", "bar") == "from-inc2"
+
     @pytest.mark.xfail(
         sys.platform == "win32",
         reason='Second config._has_includes() assertion fails (for "config is included if path is matching git_dir")',