diff --git a/tests/integrations/starlette/test_starlette.py b/tests/integrations/starlette/test_starlette.py
index 77ff368e47..ac6d1628c5 100644
--- a/tests/integrations/starlette/test_starlette.py
+++ b/tests/integrations/starlette/test_starlette.py
@@ -62,7 +62,6 @@
             starlette.datastructures.UploadFile(
                 filename="photo.jpg",
                 file=open(PICTURE, "rb"),
-                content_type="image/jpeg",
             ),
         ),
     ]
diff --git a/tox.ini b/tox.ini
index 947237ff89..5952f61709 100644
--- a/tox.ini
+++ b/tox.ini
@@ -141,7 +141,7 @@ envlist =
     {py3.7,py3.8,py3.9,py3.10,py3.11}-sanic-v{22}
 
     # Starlette
-    {py3.7,py3.8,py3.9,py3.10,py3.11}-starlette-v{0.19.1,0.20,0.21}
+    {py3.7,py3.8,py3.9,py3.10,py3.11}-starlette-v{0.20,0.22,0.24,0.26,0.28}
 
     # Starlite
     {py3.8,py3.9,py3.10,py3.11}-starlite
@@ -411,10 +411,12 @@ deps =
     starlette: pytest-asyncio
     starlette: python-multipart
     starlette: requests
-    starlette-v0.21: httpx
-    starlette-v0.19.1: starlette==0.19.1
+    starlette: httpx
     starlette-v0.20: starlette>=0.20.0,<0.21.0
-    starlette-v0.21: starlette>=0.21.0,<0.22.0
+    starlette-v0.22: starlette>=0.22.0,<0.23.0
+    starlette-v0.24: starlette>=0.24.0,<0.25.0
+    starlette-v0.26: starlette>=0.26.0,<0.27.0
+    starlette-v0.28: starlette>=0.28.0,<0.29.0
 
     # Starlite
     starlite: pytest-asyncio