diff --git a/packages/nitro/src/server/middleware.ts b/packages/nitro/src/server/middleware.ts
index 1bd25ebba9..a43efd945b 100644
--- a/packages/nitro/src/server/middleware.ts
+++ b/packages/nitro/src/server/middleware.ts
@@ -31,7 +31,7 @@ function filesToMiddleware (files: string[], baseDir: string, basePath: string,
       handle
     }
   })
-    .sort((a, b) => a.route.localeCompare(b.route))
+    .sort((a, b) => b.route.localeCompare(a.route))
     .map(m => ({ ...m, ...overrides }))
 }