diff --git a/Tests/test_imagefont.py b/Tests/test_imagefont.py
index c437e76b2..fb7987275 100644
--- a/Tests/test_imagefont.py
+++ b/Tests/test_imagefont.py
@@ -58,6 +58,9 @@ class TestImageFont(PillowTestCase):
                 ('2', '8'): {'multiline': 6.2,
                              'textsize': 2.5,
                              'getters': (12, 16)},
+                ('2', '9'): {'multiline': 6.2,
+                             'textsize': 2.5,
+                             'getters': (12, 16)},
                 'Default': {'multiline': 0.5,
                             'textsize': 0.5,
                             'getters': (12, 16)},
@@ -406,10 +409,10 @@ class TestImageFont(PillowTestCase):
         im = Image.new(mode='RGB', size=(300, 100))
         target = im.copy()
         draw = ImageDraw.Draw(im)
-        #should not crash here. 
+        #should not crash here.
         draw.text((10, 10), '', font=font)
         self.assert_image_equal(im, target)
-        
+
     def test_unicode_pilfont(self):
         # should not segfault, should return UnicodeDecodeError
         # issue #2826
diff --git a/winbuild/config.py b/winbuild/config.py
index e755577b5..1a8ef3a0b 100644
--- a/winbuild/config.py
+++ b/winbuild/config.py
@@ -34,9 +34,9 @@ libs = {
         'dir': 'tiff-4.0.9',
     },
     'freetype': {
-        'url': 'https://download.savannah.gnu.org/releases/freetype/freetype-2.8.1.tar.gz',
-        'filename': PILLOW_DEPENDS_DIR + 'freetype-2.8.1.tar.gz',
-        'dir': 'freetype-2.8.1',
+        'url': 'https://download.savannah.gnu.org/releases/freetype/freetype-2.9.tar.gz',
+        'filename': PILLOW_DEPENDS_DIR + 'freetype-2.9.tar.gz',
+        'dir': 'freetype-2.9',
     },
     'lcms': {
         'url': SF_MIRROR+'/project/lcms/lcms/2.7/lcms2-2.7.zip',