diff --git a/errors/invalid-multi-match.md b/errors/invalid-multi-match.md
new file mode 100644
index 0000000000000..cf9596b23d77a
--- /dev/null
+++ b/errors/invalid-multi-match.md
@@ -0,0 +1,27 @@
+# Invalid Multi-match
+
+#### Why This Error Occurred
+
+In one of your custom-routes you specified a multi-match `/:path*` and used it in your `destination` without adding the `*` in your `destination` e.g. `destination: '/another/:path'`
+
+#### Possible Ways to Fix It
+
+Add `*` to your usage of the multi-match param in your `destination`.
+
+**Before**
+
+```js
+{
+  source: '/:path*',
+  destination: '/another/:path'
+}
+```
+
+**After**
+
+```js
+{
+  source: '/:path*',
+  destination: '/another/:path*'
+}
+```
diff --git a/packages/next/next-server/server/next-server.ts b/packages/next/next-server/server/next-server.ts
index 104d00957c747..02e8cbf0ed459 100644
--- a/packages/next/next-server/server/next-server.ts
+++ b/packages/next/next-server/server/next-server.ts
@@ -412,7 +412,20 @@ export default class Server {
             name: `${route.type} ${route.source} route`,
             fn: async (_req, res, params, _parsedUrl) => {
               let destinationCompiler = pathToRegexp.compile(route.destination)
-              let newUrl = destinationCompiler(params)
+              let newUrl
+
+              try {
+                newUrl = destinationCompiler(params)
+              } catch (err) {
+                if (
+                  err.message.match(/Expected .*? to not repeat, but got array/)
+                ) {
+                  throw new Error(
+                    `To use a multi-match in the destination you must add \`*\` at the end of the param name to signify it should repeat. https://err.sh/zeit/next.js/invalid-multi-match`
+                  )
+                }
+                throw err
+              }
 
               if (route.type === 'redirect') {
                 res.setHeader('Location', newUrl)
diff --git a/test/integration/invalid-multi-match/next.config.js b/test/integration/invalid-multi-match/next.config.js
new file mode 100644
index 0000000000000..46cb98f27cefa
--- /dev/null
+++ b/test/integration/invalid-multi-match/next.config.js
@@ -0,0 +1,12 @@
+module.exports = {
+  experimental: {
+    rewrites() {
+      return [
+        {
+          source: '/:hello*',
+          destination: '/:hello',
+        },
+      ]
+    },
+  },
+}
diff --git a/test/integration/invalid-multi-match/pages/hello.js b/test/integration/invalid-multi-match/pages/hello.js
new file mode 100644
index 0000000000000..1b69a605b6fe9
--- /dev/null
+++ b/test/integration/invalid-multi-match/pages/hello.js
@@ -0,0 +1,15 @@
+import { useRouter } from 'next/router'
+
+console.log('hello from hello.js')
+
+const Page = () => {
+  const { query } = useRouter()
+  return (
+    <>
+      <h3>hello world</h3>
+      <span>{JSON.stringify(query)}</span>
+    </>
+  )
+}
+
+export default Page
diff --git a/test/integration/invalid-multi-match/test/index.test.js b/test/integration/invalid-multi-match/test/index.test.js
new file mode 100644
index 0000000000000..7bfddbefbb7fa
--- /dev/null
+++ b/test/integration/invalid-multi-match/test/index.test.js
@@ -0,0 +1,57 @@
+/* eslint-env jest */
+/* global jasmine */
+import { join } from 'path'
+import {
+  launchApp,
+  killApp,
+  findPort,
+  nextBuild,
+  nextStart,
+  renderViaHTTP,
+} from 'next-test-utils'
+
+jasmine.DEFAULT_TIMEOUT_INTERVAL = 1000 * 60 * 2
+
+let appDir = join(__dirname, '..')
+let stderr = ''
+let appPort
+let app
+
+const runTests = () => {
+  it('should show error for invalid mulit-match', async () => {
+    await renderViaHTTP(appPort, '/hello')
+    expect(stderr).toContain(
+      'To use a multi-match in the destination you must add'
+    )
+    expect(stderr).toContain('https://err.sh/zeit/next.js/invalid-multi-match')
+  })
+}
+
+describe('Custom routes', () => {
+  describe('dev mode', () => {
+    beforeAll(async () => {
+      appPort = await findPort()
+      app = await launchApp(appDir, appPort, {
+        onStderr: msg => {
+          stderr += msg
+        },
+      })
+    })
+    afterAll(() => killApp(app))
+    runTests(true)
+  })
+
+  describe('production mode', () => {
+    beforeAll(async () => {
+      await nextBuild(appDir)
+      appPort = await findPort()
+      app = await nextStart(appDir, appPort, {
+        onStderr: msg => {
+          stderr += msg
+        },
+      })
+    })
+    afterAll(() => killApp(app))
+    runTests()
+  })
+})