diff --git a/.github/workflows/ci.yml b/.github/workflows/ci.yml
index 1c364fe..735cacd 100644
--- a/.github/workflows/ci.yml
+++ b/.github/workflows/ci.yml
@@ -8,10 +8,11 @@ on:
 
 jobs:
   test:
-    runs-on: ubuntu-latest
+    runs-on: ${{ matrix.os }}
     strategy:
       matrix:
         python-version: ['3.13', '3.12', '3.11', '3.10', '3.9']
+        os: [ubuntu-latest, windows-latest]
     steps:
     - uses: actions/checkout@v2
     - name: Set up Python ${{ matrix.python-version }}
diff --git a/gitignore_parser.py b/gitignore_parser.py
index ef91b2b..5ccb003 100644
--- a/gitignore_parser.py
+++ b/gitignore_parser.py
@@ -4,6 +4,7 @@
 
 from os.path import abspath, dirname, join
 from pathlib import Path
+import sys
 from typing import Reversible, Union
 
 def handle_negation(file_path, rules: Reversible["IgnoreRule"]):
@@ -129,9 +130,14 @@ def __repr__(self):
     def match(self, abs_path: Union[str, Path]):
         matched = False
         if self.base_path:
-            rel_path = str(_normalize_path(abs_path).relative_to(self.base_path))
+            rel_path = _normalize_path(abs_path).relative_to(self.base_path).as_posix()
         else:
-            rel_path = str(_normalize_path(abs_path))
+            rel_path = _normalize_path(abs_path).as_posix()
+        # Path() strips the trailing following symbols on windows, so we need to
+        # preserve it: ' ', '.'
+        if sys.platform.startswith('win'):
+            rel_path += ' ' * _count_trailing_symbol(' ', abs_path)
+            rel_path += '.' * _count_trailing_symbol('.', abs_path)
         # Path() strips the trailing slash, so we need to preserve it
         # in case of directory-only negation
         if self.negation and type(abs_path) == str and abs_path[-1] == '/':
@@ -222,3 +228,14 @@ def _normalize_path(path: Union[str, Path]) -> Path:
     `Path.resolve()` does.
     """
     return Path(abspath(path))
+
+
+def _count_trailing_symbol(symbol: str, text: str) -> int:
+    """Count the number of trailing characters in a string."""
+    count = 0
+    for char in reversed(str(text)):
+        if char == symbol:
+            count += 1
+        else:
+            break
+    return count
diff --git a/tests.py b/tests.py
index bd63855..650febd 100644
--- a/tests.py
+++ b/tests.py
@@ -4,7 +4,7 @@
 
 from gitignore_parser import parse_gitignore, parse_gitignore_str
 
-from unittest import TestCase, main
+from unittest import TestCase, main, SkipTest
 
 
 class Test(TestCase):
@@ -206,13 +206,20 @@ def test_slash_in_range_does_not_match_dirs(self):
 
     def test_symlink_to_another_directory(self):
         with TemporaryDirectory() as project_dir:
+            project_dir = Path(project_dir).resolve()
             with TemporaryDirectory() as another_dir:
+                another_dir = Path(another_dir).resolve()
                 matches = parse_gitignore_str('link', base_dir=project_dir)
 
                 # Create a symlink to another directory.
-                link = Path(project_dir, 'link')
-                target = Path(another_dir, 'target')
-                link.symlink_to(target)
+                link = project_dir / 'link'
+                target = another_dir / 'target'
+                try:
+                    link.symlink_to(target)
+                except OSError:
+                    raise SkipTest(
+                        "Current user does not have permissions to perform symlink."
+                    )
 
                 # Check the intended behavior according to
                 # https://git-scm.com/docs/gitignore#_notes:
@@ -222,13 +229,19 @@ def test_symlink_to_another_directory(self):
 
     def test_symlink_to_symlink_directory(self):
         with TemporaryDirectory() as project_dir:
+            project_dir = Path(project_dir).resolve()
             with TemporaryDirectory() as link_dir:
-                link = Path(link_dir, 'link')
-                link.symlink_to(project_dir)
+                link_dir = link_dir.resolve()
+                link = link_dir / 'link'
+                try:
+                    link.symlink_to(project_dir)
+                except OSError:
+                    raise SkipTest(
+                        "Current user does not have permissions to perform symlink."
+                    )
                 file = Path(link, 'file.txt')
                 matches = parse_gitignore_str('file.txt', base_dir=str(link_dir))
                 self.assertTrue(matches(file))
 
-
 if __name__ == '__main__':
     main()