diff --git a/redirects/middleware.py b/redirects/middleware.py
index 8f957d1af..7e8546b72 100644
--- a/redirects/middleware.py
+++ b/redirects/middleware.py
@@ -1,3 +1,4 @@
+from django.db.models import CharField, F, Value
 from django.db.models.functions import Length
 from django.shortcuts import redirect
 
@@ -27,11 +28,11 @@ def __call__(self, request):
 
         # look for a direct or prefix match on the current URL
         redirection = (
-            Redirect.objects.extra(
-                where=["%s LIKE concat(old_url, '%%')"],
-                params=[request.path],
+            Redirect.objects.annotate(
+                url_length=Length("old_url"),
+                request_url=Value(request.path, output_field=CharField()),
             )
-            .annotate(url_length=Length("old_url"))
+            .filter(request_url__startswith=F("old_url"))
             .order_by("-url_length")
             .first()
         )
diff --git a/tests/unit/redirects/test_middleware.py b/tests/unit/redirects/test_middleware.py
index ebd0faf7f..c6edf6520 100644
--- a/tests/unit/redirects/test_middleware.py
+++ b/tests/unit/redirects/test_middleware.py
@@ -39,3 +39,16 @@ def test_redirectsmiddleware_unknown_url(rf):
     response = RedirectsMiddleware(get_response)(request)
 
     assert response == "no match"
+
+
+def test_redirect_with_wildcard_in_path(rf):
+    w1 = WorkspaceFactory()
+    w2 = WorkspaceFactory()
+    RedirectFactory(old_url="/abc/123/test_workspace/", workspace=w1)
+    RedirectFactory(old_url="/abc/123/test-workspace/", workspace=w2)
+
+    request = rf.get("/abc/123/test-workspace/")
+
+    response = RedirectsMiddleware(get_response)(request)
+
+    assert response.url == w2.get_absolute_url()