diff --git a/Tests/helper.py b/Tests/helper.py
index f04dffbc5..606dca006 100644
--- a/Tests/helper.py
+++ b/Tests/helper.py
@@ -267,6 +267,11 @@ class PillowLeakTestCase(PillowTestCase):
 
 py3 = sys.version_info.major >= 3
 
+if not py3:
+    # Remove DeprecationWarning in Python 3
+    PillowTestCase.assertRaisesRegex = PillowTestCase.assertRaisesRegexp
+    PillowTestCase.assertRegex = PillowTestCase.assertRegexpMatches
+
 
 def fromstring(data):
     from io import BytesIO
diff --git a/Tests/test_color_lut.py b/Tests/test_color_lut.py
index 8bf33be92..2c6c83af1 100644
--- a/Tests/test_color_lut.py
+++ b/Tests/test_color_lut.py
@@ -32,39 +32,39 @@ class TestColorLut3DCoreAPI(PillowTestCase):
     def test_wrong_args(self):
         im = Image.new('RGB', (10, 10), 0)
 
-        with self.assertRaisesRegexp(ValueError, "filter"):
+        with self.assertRaisesRegex(ValueError, "filter"):
             im.im.color_lut_3d('RGB', Image.CUBIC,
                 *self.generate_identity_table(3, 3))
 
-        with self.assertRaisesRegexp(ValueError, "image mode"):
+        with self.assertRaisesRegex(ValueError, "image mode"):
             im.im.color_lut_3d('wrong', Image.LINEAR,
                 *self.generate_identity_table(3, 3))
 
-        with self.assertRaisesRegexp(ValueError, "table_channels"):
+        with self.assertRaisesRegex(ValueError, "table_channels"):
             im.im.color_lut_3d('RGB', Image.LINEAR,
                 *self.generate_identity_table(5, 3))
 
-        with self.assertRaisesRegexp(ValueError, "table_channels"):
+        with self.assertRaisesRegex(ValueError, "table_channels"):
             im.im.color_lut_3d('RGB', Image.LINEAR,
                 *self.generate_identity_table(1, 3))
 
-        with self.assertRaisesRegexp(ValueError, "table_channels"):
+        with self.assertRaisesRegex(ValueError, "table_channels"):
             im.im.color_lut_3d('RGB', Image.LINEAR,
                 *self.generate_identity_table(2, 3))
 
-        with self.assertRaisesRegexp(ValueError, "Table size"):
+        with self.assertRaisesRegex(ValueError, "Table size"):
             im.im.color_lut_3d('RGB', Image.LINEAR,
                 *self.generate_identity_table(3, (1, 3, 3)))
 
-        with self.assertRaisesRegexp(ValueError, "Table size"):
+        with self.assertRaisesRegex(ValueError, "Table size"):
             im.im.color_lut_3d('RGB', Image.LINEAR,
                 *self.generate_identity_table(3, (66, 3, 3)))
 
-        with self.assertRaisesRegexp(ValueError, r"size1D \* size2D \* size3D"):
+        with self.assertRaisesRegex(ValueError, r"size1D \* size2D \* size3D"):
             im.im.color_lut_3d('RGB', Image.LINEAR,
                 3, 2, 2, 2, [0, 0, 0] * 7)
 
-        with self.assertRaisesRegexp(ValueError, r"size1D \* size2D \* size3D"):
+        with self.assertRaisesRegex(ValueError, r"size1D \* size2D \* size3D"):
             im.im.color_lut_3d('RGB', Image.LINEAR,
                 3, 2, 2, 2, [0, 0, 0] * 9)
 
@@ -98,27 +98,27 @@ class TestColorLut3DCoreAPI(PillowTestCase):
             *self.generate_identity_table(3, (3, 3, 65)))
 
     def test_wrong_mode(self):
-        with self.assertRaisesRegexp(ValueError, "wrong mode"):
+        with self.assertRaisesRegex(ValueError, "wrong mode"):
             im = Image.new('L', (10, 10), 0)
             im.im.color_lut_3d('RGB', Image.LINEAR,
                 *self.generate_identity_table(3, 3))
 
-        with self.assertRaisesRegexp(ValueError, "wrong mode"):
+        with self.assertRaisesRegex(ValueError, "wrong mode"):
             im = Image.new('RGB', (10, 10), 0)
             im.im.color_lut_3d('L', Image.LINEAR,
                 *self.generate_identity_table(3, 3))
 
-        with self.assertRaisesRegexp(ValueError, "wrong mode"):
+        with self.assertRaisesRegex(ValueError, "wrong mode"):
             im = Image.new('L', (10, 10), 0)
             im.im.color_lut_3d('L', Image.LINEAR,
                 *self.generate_identity_table(3, 3))
 
-        with self.assertRaisesRegexp(ValueError, "wrong mode"):
+        with self.assertRaisesRegex(ValueError, "wrong mode"):
             im = Image.new('RGB', (10, 10), 0)
             im.im.color_lut_3d('RGBA', Image.LINEAR,
                 *self.generate_identity_table(3, 3))
 
-        with self.assertRaisesRegexp(ValueError, "wrong mode"):
+        with self.assertRaisesRegex(ValueError, "wrong mode"):
             im = Image.new('RGB', (10, 10), 0)
             im.im.color_lut_3d('RGB', Image.LINEAR,
                 *self.generate_identity_table(4, 3))
@@ -238,31 +238,31 @@ class TestColorLut3DCoreAPI(PillowTestCase):
 
 class TestColorLut3DFilter(PillowTestCase):
     def test_wrong_args(self):
-        with self.assertRaisesRegexp(ValueError, "should be either an integer"):
+        with self.assertRaisesRegex(ValueError, "should be either an integer"):
             ImageFilter.Color3DLUT("small", [1])
 
-        with self.assertRaisesRegexp(ValueError, "should be either an integer"):
+        with self.assertRaisesRegex(ValueError, "should be either an integer"):
             ImageFilter.Color3DLUT((11, 11), [1])
 
-        with self.assertRaisesRegexp(ValueError, r"in \[2, 65\] range"):
+        with self.assertRaisesRegex(ValueError, r"in \[2, 65\] range"):
             ImageFilter.Color3DLUT((11, 11, 1), [1])
 
-        with self.assertRaisesRegexp(ValueError, r"in \[2, 65\] range"):
+        with self.assertRaisesRegex(ValueError, r"in \[2, 65\] range"):
             ImageFilter.Color3DLUT((11, 11, 66), [1])
 
-        with self.assertRaisesRegexp(ValueError, "table should have .+ items"):
+        with self.assertRaisesRegex(ValueError, "table should have .+ items"):
             ImageFilter.Color3DLUT((3, 3, 3), [1, 1, 1])
 
-        with self.assertRaisesRegexp(ValueError, "table should have .+ items"):
+        with self.assertRaisesRegex(ValueError, "table should have .+ items"):
             ImageFilter.Color3DLUT((3, 3, 3), [[1, 1, 1]] * 2)
 
-        with self.assertRaisesRegexp(ValueError, "should have a length of 4"):
+        with self.assertRaisesRegex(ValueError, "should have a length of 4"):
             ImageFilter.Color3DLUT((3, 3, 3), [[1, 1, 1]] * 27, channels=4)
 
-        with self.assertRaisesRegexp(ValueError, "should have a length of 3"):
+        with self.assertRaisesRegex(ValueError, "should have a length of 3"):
             ImageFilter.Color3DLUT((2, 2, 2), [[1, 1]] * 8)
 
-        with self.assertRaisesRegexp(ValueError, "Only 3 or 4 output"):
+        with self.assertRaisesRegex(ValueError, "Only 3 or 4 output"):
             ImageFilter.Color3DLUT((2, 2, 2), [[1, 1]] * 8, channels=2)
 
     def test_convert_table(self):
@@ -290,16 +290,17 @@ class TestColorLut3DFilter(PillowTestCase):
         self.assertEqual(repr(lut),
             "<Color3DLUT from array size=3x4x5 channels=4 target_mode=YCbCr>")
 
+
 class TestGenerateColorLut3D(PillowTestCase):
     def test_wrong_channels_count(self):
-        with self.assertRaisesRegexp(ValueError, "3 or 4 output channels"):
+        with self.assertRaisesRegex(ValueError, "3 or 4 output channels"):
             ImageFilter.Color3DLUT.generate(5, channels=2,
                 callback=lambda r, g, b: (r, g, b))
 
-        with self.assertRaisesRegexp(ValueError, "should have either channels"):
+        with self.assertRaisesRegex(ValueError, "should have either channels"):
             ImageFilter.Color3DLUT.generate(5, lambda r, g, b: (r, g, b, r))
 
-        with self.assertRaisesRegexp(ValueError, "should have either channels"):
+        with self.assertRaisesRegex(ValueError, "should have either channels"):
             ImageFilter.Color3DLUT.generate(5, channels=4,
                 callback=lambda r, g, b: (r, g, b))
 
@@ -333,13 +334,13 @@ class TestTransformColorLut3D(PillowTestCase):
     def test_wrong_args(self):
         source = ImageFilter.Color3DLUT.generate(5, lambda r, g, b: (r, g, b))
 
-        with self.assertRaisesRegexp(ValueError, "Only 3 or 4 output"):
+        with self.assertRaisesRegex(ValueError, "Only 3 or 4 output"):
             source.transform(lambda r, g, b: (r, g, b), channels=8)
 
-        with self.assertRaisesRegexp(ValueError, "should have either channels"):
+        with self.assertRaisesRegex(ValueError, "should have either channels"):
             source.transform(lambda r, g, b: (r, g, b), channels=4)
 
-        with self.assertRaisesRegexp(ValueError, "should have either channels"):
+        with self.assertRaisesRegex(ValueError, "should have either channels"):
             source.transform(lambda r, g, b: (r, g, b, 1))
 
         with self.assertRaises(TypeError):
diff --git a/Tests/test_file_jpeg.py b/Tests/test_file_jpeg.py
index 205a6ffdf..e7e639f05 100644
--- a/Tests/test_file_jpeg.py
+++ b/Tests/test_file_jpeg.py
@@ -41,7 +41,7 @@ class TestFileJpeg(PillowTestCase):
     def test_sanity(self):
 
         # internal version number
-        self.assertRegexpMatches(Image.core.jpeglib_version, r"\d+\.\d+$")
+        self.assertRegex(Image.core.jpeglib_version, r"\d+\.\d+$")
 
         im = Image.open(TEST_FILE)
         im.load()
diff --git a/Tests/test_file_jpeg2k.py b/Tests/test_file_jpeg2k.py
index 810e21a9d..71f15f7b8 100644
--- a/Tests/test_file_jpeg2k.py
+++ b/Tests/test_file_jpeg2k.py
@@ -31,7 +31,7 @@ class TestFileJpeg2k(PillowTestCase):
 
     def test_sanity(self):
         # Internal version number
-        self.assertRegexpMatches(Image.core.jp2klib_version, r'\d+\.\d+\.\d+$')
+        self.assertRegex(Image.core.jp2klib_version, r'\d+\.\d+\.\d+$')
 
         im = Image.open('Tests/images/test-card-lossless.jp2')
         px = im.load()
diff --git a/Tests/test_file_png.py b/Tests/test_file_png.py
index 8cf109e70..abf3f2953 100644
--- a/Tests/test_file_png.py
+++ b/Tests/test_file_png.py
@@ -68,8 +68,7 @@ class TestFilePng(PillowTestCase):
     def test_sanity(self):
 
         # internal version number
-        self.assertRegexpMatches(
-            Image.core.zlib_version, r"\d+\.\d+\.\d+(\.\d+)?$")
+        self.assertRegex(Image.core.zlib_version, r"\d+\.\d+\.\d+(\.\d+)?$")
 
         test_file = self.tempfile("temp.png")
 
diff --git a/Tests/test_image_resample.py b/Tests/test_image_resample.py
index 4223db530..1ecb6cda6 100644
--- a/Tests/test_image_resample.py
+++ b/Tests/test_image_resample.py
@@ -383,24 +383,24 @@ class CoreResampleBoxTest(PillowTestCase):
             im.resize((32, 32), resample, (20, 20, 20, 100))
             im.resize((32, 32), resample, (20, 20, 100, 20))
 
-            with self.assertRaisesRegexp(TypeError, "must be sequence of length 4"):
+            with self.assertRaisesRegex(TypeError, "must be sequence of length 4"):
                 im.resize((32, 32), resample, (im.width, im.height))
 
-            with self.assertRaisesRegexp(ValueError, "can't be negative"):
+            with self.assertRaisesRegex(ValueError, "can't be negative"):
                 im.resize((32, 32), resample, (-20, 20, 100, 100))
-            with self.assertRaisesRegexp(ValueError, "can't be negative"):
+            with self.assertRaisesRegex(ValueError, "can't be negative"):
                 im.resize((32, 32), resample, (20, -20, 100, 100))
 
-            with self.assertRaisesRegexp(ValueError, "can't be empty"):
+            with self.assertRaisesRegex(ValueError, "can't be empty"):
                 im.resize((32, 32), resample, (20.1, 20, 20, 100))
-            with self.assertRaisesRegexp(ValueError, "can't be empty"):
+            with self.assertRaisesRegex(ValueError, "can't be empty"):
                 im.resize((32, 32), resample, (20, 20.1, 100, 20))
-            with self.assertRaisesRegexp(ValueError, "can't be empty"):
+            with self.assertRaisesRegex(ValueError, "can't be empty"):
                 im.resize((32, 32), resample, (20.1, 20.1, 20, 20))
 
-            with self.assertRaisesRegexp(ValueError, "can't exceed"):
+            with self.assertRaisesRegex(ValueError, "can't exceed"):
                 im.resize((32, 32), resample, (0, 0, im.width + 1, im.height))
-            with self.assertRaisesRegexp(ValueError, "can't exceed"):
+            with self.assertRaisesRegex(ValueError, "can't exceed"):
                 im.resize((32, 32), resample, (0, 0, im.width, im.height + 1))
 
     def resize_tiled(self, im, dst_size, xtiles, ytiles):
@@ -447,7 +447,7 @@ class CoreResampleBoxTest(PillowTestCase):
 
         # error with box should be much smaller than without
         self.assert_image_similar(reference, with_box, 6)
-        with self.assertRaisesRegexp(AssertionError, "difference 29\."):
+        with self.assertRaisesRegex(AssertionError, "difference 29\."):
             self.assert_image_similar(reference, without_box, 5)
 
     def test_formats(self):
@@ -490,7 +490,7 @@ class CoreResampleBoxTest(PillowTestCase):
             try:
                 res = im.resize(size, Image.LANCZOS, box)
                 self.assertEqual(res.size, size)
-                with self.assertRaisesRegexp(AssertionError, "difference \d"):
+                with self.assertRaisesRegex(AssertionError, "difference \d"):
                     # check that the difference at least that much
                     self.assert_image_similar(res, im.crop(box), 20)
             except AssertionError:
diff --git a/Tests/test_imagecms.py b/Tests/test_imagecms.py
index 31417564f..4138f455f 100644
--- a/Tests/test_imagecms.py
+++ b/Tests/test_imagecms.py
@@ -43,7 +43,7 @@ class TestImageCms(PillowTestCase):
         self.assertEqual(list(map(type, v)), [str, str, str, str])
 
         # internal version number
-        self.assertRegexpMatches(ImageCms.core.littlecms_version, r"\d+\.\d+$")
+        self.assertRegex(ImageCms.core.littlecms_version, r"\d+\.\d+$")
 
         self.skip_missing()
         i = ImageCms.profileToProfile(hopper(), SRGB, SRGB)
diff --git a/Tests/test_imagefont.py b/Tests/test_imagefont.py
index 0ec49384e..986b0b5ef 100644
--- a/Tests/test_imagefont.py
+++ b/Tests/test_imagefont.py
@@ -75,8 +75,7 @@ class TestImageFont(PillowTestCase):
                                   layout_engine=self.LAYOUT_ENGINE)
 
     def test_sanity(self):
-        self.assertRegexpMatches(
-            ImageFont.core.freetype2_version, r"\d+\.\d+\.\d+$")
+        self.assertRegex(ImageFont.core.freetype2_version, r"\d+\.\d+\.\d+$")
 
     def test_font_properties(self):
         ttf = self.get_font()