diff --git a/runtime_tests/bun/index.test.tsx b/runtime_tests/bun/index.test.tsx
index 9aaaf26d0..db2f7edd1 100644
--- a/runtime_tests/bun/index.test.tsx
+++ b/runtime_tests/bun/index.test.tsx
@@ -145,6 +145,18 @@ describe('Serve Static Middleware', () => {
     expect(res.status).toBe(200)
     expect(await res.text()).toBe('Bun!!')
   })
+
+  it('Should return 200 response - /static/helloworld', async () => {
+    const res = await app.request('http://localhost/static/helloworld')
+    expect(res.status).toBe(200)
+    expect(await res.text()).toBe('Hi\n')
+  })
+
+  it('Should return 200 response - /static/hello.world', async () => {
+    const res = await app.request('http://localhost/static/hello.world')
+    expect(res.status).toBe(200)
+    expect(await res.text()).toBe('Hi\n')
+  })
 })
 
 // Bun support WebCrypto since v0.2.2
diff --git a/runtime_tests/bun/static/hello.world/index.html b/runtime_tests/bun/static/hello.world/index.html
new file mode 100644
index 000000000..b14df6442
--- /dev/null
+++ b/runtime_tests/bun/static/hello.world/index.html
@@ -0,0 +1 @@
+Hi
diff --git a/runtime_tests/bun/static/helloworld/index.html b/runtime_tests/bun/static/helloworld/index.html
new file mode 100644
index 000000000..b14df6442
--- /dev/null
+++ b/runtime_tests/bun/static/helloworld/index.html
@@ -0,0 +1 @@
+Hi
diff --git a/runtime_tests/deno/middleware.test.tsx b/runtime_tests/deno/middleware.test.tsx
index 534160c54..aed22e28a 100644
--- a/runtime_tests/deno/middleware.test.tsx
+++ b/runtime_tests/deno/middleware.test.tsx
@@ -123,6 +123,14 @@ Deno.test('Serve Static middleware', async () => {
   } as Request)
   assertEquals(res.status, 404)
   assertEquals(await res.text(), '404 Not Found')
+
+  res = await app.request('http://localhost/static/helloworld')
+  assertEquals(res.status, 200)
+  assertEquals(await res.text(), 'Hi\n')
+
+  res = await app.request('http://localhost/static/hello.world')
+  assertEquals(res.status, 200)
+  assertEquals(await res.text(), 'Hi\n')
 })
 
 Deno.test('JWT Authentication middleware', async () => {
diff --git a/runtime_tests/deno/static/hello.world/index.html b/runtime_tests/deno/static/hello.world/index.html
new file mode 100644
index 000000000..b14df6442
--- /dev/null
+++ b/runtime_tests/deno/static/hello.world/index.html
@@ -0,0 +1 @@
+Hi
diff --git a/runtime_tests/deno/static/helloworld/index.html b/runtime_tests/deno/static/helloworld/index.html
new file mode 100644
index 000000000..b14df6442
--- /dev/null
+++ b/runtime_tests/deno/static/helloworld/index.html
@@ -0,0 +1 @@
+Hi
diff --git a/src/adapter/bun/serve-static.ts b/src/adapter/bun/serve-static.ts
index 768dffef8..be9fa2cca 100644
--- a/src/adapter/bun/serve-static.ts
+++ b/src/adapter/bun/serve-static.ts
@@ -2,6 +2,7 @@
 import { serveStatic as baseServeStatic } from '../../middleware/serve-static'
 import type { ServeStaticOptions } from '../../middleware/serve-static'
 import type { Env, MiddlewareHandler } from '../../types'
+import { stat } from 'node:fs/promises'
 
 export const serveStatic = <E extends Env = Env>(
   options: ServeStaticOptions<E>
@@ -16,10 +17,19 @@ export const serveStatic = <E extends Env = Env>(
     const pathResolve = (path: string) => {
       return `./${path}`
     }
+    const isDir = async (path: string) => {
+      let isDir
+      try {
+        const stats = await stat(path)
+        isDir = stats.isDirectory()
+      } catch {}
+      return isDir
+    }
     return baseServeStatic({
       ...options,
       getContent,
       pathResolve,
+      isDir,
     })(c, next)
   }
 }
diff --git a/src/adapter/deno/serve-static.ts b/src/adapter/deno/serve-static.ts
index b037466b6..056fae025 100644
--- a/src/adapter/deno/serve-static.ts
+++ b/src/adapter/deno/serve-static.ts
@@ -4,7 +4,7 @@ import type { Env, MiddlewareHandler } from '../../types'
 
 // eslint-disable-next-line @typescript-eslint/ban-ts-comment
 // @ts-ignore
-const { open } = Deno
+const { open, lstatSync } = Deno
 
 export const serveStatic = <E extends Env = Env>(
   options: ServeStaticOptions<E>
@@ -22,10 +22,19 @@ export const serveStatic = <E extends Env = Env>(
     const pathResolve = (path: string) => {
       return `./${path}`
     }
+    const isDir = (path: string) => {
+      let isDir
+      try {
+        const stat = lstatSync(path)
+        isDir = stat.isDirectory
+      } catch {}
+      return isDir
+    }
     return baseServeStatic({
       ...options,
       getContent,
       pathResolve,
+      isDir,
     })(c, next)
   }
 }
diff --git a/src/middleware/serve-static/index.test.ts b/src/middleware/serve-static/index.test.ts
index ca611b67b..efae1aeb5 100644
--- a/src/middleware/serve-static/index.test.ts
+++ b/src/middleware/serve-static/index.test.ts
@@ -15,6 +15,9 @@ describe('Serve Static Middleware', () => {
     pathResolve: (path) => {
       return `./${path}`
     },
+    isDir: (path) => {
+      return path === 'static/hello.world'
+    },
   })
 
   app.get('/static/*', serveStatic)
@@ -37,6 +40,20 @@ describe('Serve Static Middleware', () => {
     expect(await res.text()).toBe('Hello in ./static/sub/index.html')
   })
 
+  it('Should return 200 response - /static/helloworld', async () => {
+    const res = await app.request('/static/helloworld')
+    expect(res.status).toBe(200)
+    expect(res.headers.get('Content-Type')).toMatch(/^text\/html/)
+    expect(await res.text()).toBe('Hello in ./static/helloworld/index.html')
+  })
+
+  it('Should return 200 response - /static/hello.world', async () => {
+    const res = await app.request('/static/hello.world')
+    expect(res.status).toBe(200)
+    expect(res.headers.get('Content-Type')).toMatch(/^text\/html/)
+    expect(await res.text()).toBe('Hello in ./static/hello.world/index.html')
+  })
+
   it('Should decode URI strings - /static/%E7%82%8E.txt', async () => {
     const res = await app.request('/static/%E7%82%8E.txt')
     expect(res.status).toBe(200)
diff --git a/src/middleware/serve-static/index.ts b/src/middleware/serve-static/index.ts
index 134f4c444..1e3e78569 100644
--- a/src/middleware/serve-static/index.ts
+++ b/src/middleware/serve-static/index.ts
@@ -26,6 +26,7 @@ export const serveStatic = <E extends Env = Env>(
   options: ServeStaticOptions<E> & {
     getContent: (path: string, c: Context<E>) => Promise<Data | Response | null>
     pathResolve?: (path: string) => string
+    isDir?: (path: string) => boolean | undefined | Promise<boolean | undefined>
   }
 ): MiddlewareHandler => {
   return async (c, next) => {
@@ -39,6 +40,17 @@ export const serveStatic = <E extends Env = Env>(
     filename = options.rewriteRequestPath ? options.rewriteRequestPath(filename) : filename
     const root = options.root
 
+    // If it was Directory, force `/` on the end.
+    if (!filename.endsWith('/') && options.isDir) {
+      const path = getFilePathWithoutDefaultDocument({
+        filename,
+        root,
+      })
+      if (path && (await options.isDir(path))) {
+        filename = filename + '/'
+      }
+    }
+
     let path = getFilePath({
       filename,
       root,