diff --git a/src/framework/openapi.spec.loader.ts b/src/framework/openapi.spec.loader.ts
index f96374aa..9ce6cbee 100644
--- a/src/framework/openapi.spec.loader.ts
+++ b/src/framework/openapi.spec.loader.ts
@@ -33,6 +33,8 @@ interface DiscoveredRoutes {
 export const sortRoutes = (r1, r2) => {
   const e1 = r1.expressRoute.replace(/\/:/g, '/~');
   const e2 = r2.expressRoute.replace(/\/:/g, '/~');
+  if (e1.startsWith(e2)) return -1;
+  else if (e2.startsWith(e1)) return 1;
   return e1 > e2 ? 1 : -1;
 };
 
diff --git a/test/1022.spec.ts b/test/1022.spec.ts
new file mode 100644
index 00000000..a28cac8a
--- /dev/null
+++ b/test/1022.spec.ts
@@ -0,0 +1,130 @@
+import * as express from 'express';
+import * as request from 'supertest';
+import { createApp } from './common/app';
+import * as packageJson from '../package.json';
+import { OpenAPIV3 } from '../src/framework/types';
+import {expect} from "chai";
+
+describe(packageJson.name, () => {
+  let app = null;
+  before(async () => {
+    // Set up the express app
+    const apiSpec: OpenAPIV3.DocumentV3 = {
+      openapi: '3.0.0',
+      info: { title: 'Api test', version: '1.0.0' },
+      servers: [{ url: '/api' }],
+      paths: {
+        '/test/{id}': {
+          description: 'Description',
+          parameters: [
+            {
+              name: 'id',
+              in: 'path',
+              required: true,
+              schema: { type: 'string' },
+            },
+          ],
+          get: {
+            responses: {
+              '200': {
+                description: 'response',
+                content: {
+                  'application/json': {
+                    schema: {
+                      type: 'object',
+                      properties: {
+                        id: { type: 'string' },
+                        label: { type: 'string' },
+                      },
+                    },
+                  },
+                },
+              },
+            },
+          },
+        },
+        '/test/{id}:clone': {
+          description: 'Description',
+          parameters: [
+            {
+              name: 'id',
+              in: 'path',
+              required: true,
+              schema: { type: 'string' },
+            },
+          ],
+
+          post: {
+            requestBody: {
+              content: {
+                'application/json': {
+                  schema: {
+                    type: 'object',
+                    required: ['id'],
+                    properties: {
+                      id: {
+                        type: 'integer'
+                      }
+                    }
+                  }
+                }
+              }
+            },
+            responses: {
+              '200': {
+                description: 'response',
+                content: {
+                  'application/json': {
+                    schema: {
+                      type: 'object',
+                      properties: {
+                        id: { type: 'string' },
+                        label: { type: 'string' },
+                      },
+                    },
+                  },
+                },
+              },
+            },
+          },
+        },
+      },
+    };
+
+    app = await createApp(
+      {
+        apiSpec,
+        validateRequests: true,
+        validateResponses: true,
+      },
+      3005,
+      (app) =>
+        app.use(
+          express
+            .Router()
+            .get(`/api/test/:id`, (req, res) => res.status(200).json({ id: 'id-test', label: 'label'}))
+            .post(`/api/test/:id:clone`, (req, res) => res.status(200).json({...req.body, id: 'id-test'})),
+        ),
+    );
+  });
+
+  after(() => {
+    app.server.close();
+  });
+
+  it('get /test/{id} should return 200', async () =>
+    request(app).get(`/api/test/abc123`).expect(200));
+
+  it('POST /test/{id}:clone should return 200', async () =>
+    request(app).post(`/api/test/abc123:clone`)
+        .send({ id: 10 })
+        .expect(200));
+
+  it('POST /test/{id}:clone should return 400', async () =>
+    request(app).post(`/api/test/abc123:clone`)
+        .send({ id: 'abc123' })
+        .expect(400)
+        .then(r => {
+          expect(r.body.message).to.include('id must be integer');
+        }));
+});