diff --git a/packages/vite/src/node/server/middlewares/indexHtml.ts b/packages/vite/src/node/server/middlewares/indexHtml.ts
index 54351a937c8e1f..7aa2ba7aaa401e 100644
--- a/packages/vite/src/node/server/middlewares/indexHtml.ts
+++ b/packages/vite/src/node/server/middlewares/indexHtml.ts
@@ -114,6 +114,10 @@ function shouldPreTransform(url: string, config: ResolvedConfig) {
 
 const wordCharRE = /\w/
 
+function isBareRelative(url: string) {
+  return wordCharRE.test(url[0]) && !url.includes(':')
+}
+
 const isSrcSet = (attr: Token.Attribute) =>
   attr.name === 'srcset' && attr.prefix === undefined
 const processNodeUrl = (
@@ -143,20 +147,30 @@ const processNodeUrl = (
       // rewrite `./index.js` -> `localhost:5173/a/index.js`.
       // rewrite `../index.js` -> `localhost:5173/index.js`.
       // rewrite `relative/index.js` -> `localhost:5173/a/relative/index.js`.
-      ((url[0] === '.' || (wordCharRE.test(url[0]) && !url.includes(':'))) &&
+      ((url[0] === '.' || isBareRelative(url)) &&
         originalUrl &&
         originalUrl !== '/' &&
         htmlPath === '/index.html')
     ) {
-      const devBase = config.base
-      const fullUrl = path.posix.join(devBase, url)
-      if (server && shouldPreTransform(url, config)) {
-        preTransformRequest(server, fullUrl, devBase)
+      url = path.posix.join(config.base, url)
+    }
+
+    if (server && shouldPreTransform(url, config)) {
+      let preTransformUrl: string | undefined
+      if (url[0] === '/') {
+        preTransformUrl = url
+      } else if (url[0] === '.' || isBareRelative(url)) {
+        preTransformUrl = path.posix.join(
+          config.base,
+          path.posix.dirname(htmlPath),
+          url,
+        )
+      }
+      if (preTransformUrl) {
+        preTransformRequest(server, preTransformUrl, config.base)
       }
-      return fullUrl
-    } else {
-      return url
     }
+    return url
   }
 
   const processedUrl = useSrcSetReplacer