diff --git a/flow/declarations.js b/flow/declarations.js
index 824c3eca0..8377f789f 100644
--- a/flow/declarations.js
+++ b/flow/declarations.js
@@ -77,6 +77,7 @@ declare type RouteRecord = {
   beforeEnter: ?NavigationGuard;
   meta: any;
   props: boolean | Object | Function | Dictionary<boolean | Object | Function>;
+  pathToRegexpOptions: PathToRegexpOptions;
 }
 
 declare type Location = {
diff --git a/src/create-matcher.js b/src/create-matcher.js
index f7d72b93e..306294e7b 100644
--- a/src/create-matcher.js
+++ b/src/create-matcher.js
@@ -22,14 +22,18 @@ export function createMatcher (
 ): Matcher {
   const { pathList, pathMap, nameMap } = createRouteMap(routes)
 
+  let _optimizedMatcher = optimizedMatcher(pathList, pathMap)
+
   function addRoutes (routes) {
     createRouteMap(routes, pathList, pathMap, nameMap)
+    _optimizedMatcher = optimizedMatcher(pathList, pathMap)
   }
 
   function addRoute (parentOrRoute, route) {
     const parent = (typeof parentOrRoute !== 'object') ? nameMap[parentOrRoute] : undefined
     // $flow-disable-line
     createRouteMap([route || parentOrRoute], pathList, pathMap, nameMap, parent)
+    _optimizedMatcher = optimizedMatcher(pathList, pathMap)
 
     // add aliases of parent
     if (parent && parent.alias.length) {
@@ -82,12 +86,9 @@ export function createMatcher (
       return _createRoute(record, location, redirectedFrom)
     } else if (location.path) {
       location.params = {}
-      for (let i = 0; i < pathList.length; i++) {
-        const path = pathList[i]
-        const record = pathMap[path]
-        if (matchRoute(record.regex, location.path, location.params)) {
-          return _createRoute(record, location, redirectedFrom)
-        }
+      const record = _optimizedMatcher(location.path, location.params)
+      if (record) {
+        return _createRoute(record, location, redirectedFrom)
       }
     }
     // no match
@@ -224,3 +225,82 @@ function matchRoute (
 function resolveRecordPath (path: string, record: RouteRecord): string {
   return resolvePath(path, record.parent ? record.parent.path : '/', true)
 }
+
+function isStatic (route) {
+  return (
+    // Custom regex options are dynamic.
+    Object.keys(route.pathToRegexpOptions).length === 0 &&
+    // Dynamic paths have /:placeholder or anonymous placeholder /(.+) or wildcard *.
+    !/[:(*]/.exec(route.path)
+  )
+}
+
+function firstLevelStatic (path) {
+  // firstLevel = ['/p/', '/p', '/' index: 0, input: '/p/b/c', groups: undefined]
+  const firstLevel = /^(\/[^:(*/]+)(\/|$)/.exec(path)
+  return firstLevel && firstLevel[1]
+}
+
+function optimizedMatcher (
+  pathList: Array<string>,
+  pathMap: Dictionary<RouteRecord>
+) {
+  // Lookup table
+  // e.g. Route /p/b is mapped as {"/p/b": route}
+  const staticMap = {}
+  // Buckets with the first level static path.
+  // e.g. Route /p/b/:id is mapped as {"/p": [route]}
+  const firstLevelStaticMap = {}
+  // Array of everything else.
+  const dynamic = []
+
+  pathList.forEach((path, index) => {
+    const route = pathMap[path]
+    const normalizedPath = route.regex.ignoreCase ? path.toLowerCase() : path
+    if (isStatic(route)) {
+      staticMap[normalizedPath] = { index, route }
+    } else {
+      const firstLevel = firstLevelStatic(path.toLowerCase())
+      if (firstLevel) {
+        if (!firstLevelStaticMap[firstLevel]) {
+          firstLevelStaticMap[firstLevel] = []
+        }
+        firstLevelStaticMap[firstLevel].push({ index, route })
+      } else {
+        dynamic.push({ index, route })
+      }
+    }
+  })
+
+  function match (path, params) {
+    const cleanPath = path.replace(/\/$/, '').toLowerCase()
+    let record = staticMap[cleanPath]
+
+    const firstLevel = firstLevelStatic(path)
+    const firstLevelRoutes = firstLevelStaticMap[firstLevel] || []
+
+    for (let i = 0; i < firstLevelRoutes.length; i++) {
+      const { index, route } = firstLevelRoutes[i]
+      if (record && index >= record.index) {
+        break
+      }
+      if (matchRoute(route.regex, path, params)) {
+        record = firstLevelRoutes[i]
+        break
+      }
+    }
+
+    for (let j = 0; j < dynamic.length; j++) {
+      const { index, route } = dynamic[j]
+      if (record && index >= record.index) {
+        break
+      }
+      if (matchRoute(route.regex, path, params)) {
+        record = dynamic[j]
+      }
+    }
+    return record && record.route
+  }
+
+  return match
+}
diff --git a/src/create-route-map.js b/src/create-route-map.js
index 93a558f8a..61affa3f1 100644
--- a/src/create-route-map.js
+++ b/src/create-route-map.js
@@ -92,6 +92,7 @@ function addRouteRecord (
   const record: RouteRecord = {
     path: normalizedPath,
     regex: compileRouteRegex(normalizedPath, pathToRegexpOptions),
+    pathToRegexpOptions,
     components: route.components || { default: route.component },
     alias: route.alias
       ? typeof route.alias === 'string'
diff --git a/test/unit/specs/create-matcher.spec.js b/test/unit/specs/create-matcher.spec.js
index fcc2587c2..97da43b51 100644
--- a/test/unit/specs/create-matcher.spec.js
+++ b/test/unit/specs/create-matcher.spec.js
@@ -151,4 +151,163 @@ describe('Creating Matcher', function () {
     expect(pathForErrorRoute).toEqual('/error/')
     expect(pathForNotFoundRoute).toEqual('/')
   })
+
+  it('respect ordering', function () {
+    const matcher = createMatcher([
+      {
+        path: '/p/staticbefore',
+        name: 'staticbefore',
+        component: { name: 'staticbefore' }
+      },
+      {
+        path: '/p/:id',
+        name: 'dynamic',
+        component: { name: 'dynamic' }
+      },
+      {
+        path: '/p/staticafter',
+        name: 'staticafter',
+        component: { name: 'staticafter' }
+      }
+    ])
+    expect(matcher.match('/p/staticbefore').name).toBe('staticbefore')
+    expect(matcher.match('/p/staticafter').name).toBe('dynamic')
+  })
+
+  it('respect ordering for full dynamic', function () {
+    const matcher = createMatcher([
+      {
+        path: '/before/static',
+        name: 'staticbefore',
+        component: { name: 'staticbefore' }
+      },
+      {
+        path: '/:foo/static',
+        name: 'dynamic',
+        component: { name: 'dynamic' }
+      },
+      {
+        path: '/after/static',
+        name: 'staticafter',
+        component: { name: 'staticafter' }
+      }
+    ])
+    expect(matcher.match('/before/static').name).toBe('staticbefore')
+    expect(matcher.match('/after/static').name).toBe('dynamic')
+  })
+
+  it('respect ordering between full dynamic and first level static', function () {
+    const matcher = createMatcher([
+      {
+        path: '/before/:foo',
+        name: 'staticbefore',
+        component: { name: 'staticbefore' }
+      },
+      {
+        path: '/:foo/static',
+        name: 'dynamic',
+        component: { name: 'dynamic' }
+      },
+      {
+        path: '/after/:foo',
+        name: 'staticafter',
+        component: { name: 'staticafter' }
+      }
+    ])
+    expect(matcher.match('/before/static').name).toBe('staticbefore')
+    expect(matcher.match('/after/static').name).toBe('dynamic')
+  })
+
+  it('static can use sensitive flag', function () {
+    const matcher = createMatcher([
+      {
+        path: '/p/sensitive',
+        name: 'sensitive',
+        pathToRegexpOptions: {
+          sensitive: true
+        },
+        component: { name: 'sensitive' }
+      },
+      {
+        path: '/p/insensitive',
+        name: 'insensitive',
+        component: { name: 'insensitive' }
+      },
+      {
+        path: '*', name: 'not-found', component: { name: 'not-found ' }
+      }
+    ])
+
+    expect(matcher.match('/p/SENSITIVE').name).toBe('not-found')
+    expect(matcher.match('/p/INSENSITIVE').name).toBe('insensitive')
+  })
+
+  it('static can use strict flag', function () {
+    const matcher = createMatcher([
+      {
+        path: '/p/strict',
+        name: 'strict',
+        pathToRegexpOptions: {
+          strict: true
+        },
+        component: { name: 'strict' }
+      },
+      {
+        path: '/p/unstrict',
+        name: 'unstrict',
+        component: { name: 'unstrict' }
+      },
+      {
+        path: '*', name: 'not-found', component: { name: 'not-found ' }
+      }
+    ])
+
+    expect(matcher.match('/p/strict/').name).toBe('not-found')
+    expect(matcher.match('/p/unstrict/').name).toBe('unstrict')
+  })
+
+  it('static can use end flag', function () {
+    const matcher = createMatcher([
+      {
+        path: '/p/end',
+        name: 'end',
+        component: { name: 'end' }
+      },
+      {
+        path: '/p/not-end',
+        name: 'not-end',
+        pathToRegexpOptions: {
+          end: false
+        },
+        component: { name: 'not-end' }
+      },
+      {
+        path: '*', name: 'not-found', component: { name: 'not-found ' }
+      }
+    ])
+
+    expect(matcher.match('/p/end/foo').name).toBe('not-found')
+    expect(matcher.match('/p/not-end/foo').name).toBe('not-end')
+  })
+
+  it('first level dynamic must work', function () {
+    const matcher = createMatcher([
+      {
+        path: '/:foo/b',
+        name: 'b',
+        component: { name: 'b' }
+      },
+      {
+        path: '/p/c',
+        name: 'c',
+        component: { name: 'c' }
+      },
+      {
+        path: '*', name: 'not-found', component: { name: 'not-found ' }
+      }
+    ])
+
+    expect(matcher.match('/p/b').name).toBe('b')
+    expect(matcher.match('/p/c').name).toBe('c')
+  })
 })
diff --git a/test/unit/specs/error-handling.spec.js b/test/unit/specs/error-handling.spec.js
index 52d61e210..a9b8e11e8 100644
--- a/test/unit/specs/error-handling.spec.js
+++ b/test/unit/specs/error-handling.spec.js
@@ -5,6 +5,10 @@ import { NavigationFailureType } from '../../../src/util/errors'
 Vue.use(VueRouter)
 
 describe('error handling', () => {
+  beforeEach(function () {
+    process.env.NODE_ENV = 'development'
+  })
+
   it('onReady errors', done => {
     const router = new VueRouter()
     const err = new Error('foo')
diff --git a/types/router.d.ts b/types/router.d.ts
index f8588f42f..4c5b63f3f 100644
--- a/types/router.d.ts
+++ b/types/router.d.ts
@@ -147,6 +147,7 @@ export type RouteConfig = RouteConfigSingleView | RouteConfigMultipleViews
 export interface RouteRecord {
   path: string
   regex: RegExp
+  pathToRegexpOptions: PathToRegexpOptions
   components: Dictionary<Component>
   instances: Dictionary<Vue>
   name?: string