diff --git a/src/index.coffee b/src/index.coffee
index ccf6806..666bfa4 100644
--- a/src/index.coffee
+++ b/src/index.coffee
@@ -21,10 +21,15 @@ module.exports = (patterns = [], options = {}) ->
       file.relative
 
   rank = (s) ->
-    for matcher, index in matchers
-      return index if matcher.match s
+    indexes = matchers.map (matcher, index) ->
+      if matcher.match s then index else undefined
+    .filter (index) ->
+      index?
 
-    return matchers.length
+    if indexes.length
+      indexes[indexes.length - 1]
+    else
+      matchers.length
 
   onEnd = ->
     sort.inplace files, (a, b) ->
diff --git a/test/tests.coffee b/test/tests.coffee
index a48a423..7cdf64a 100644
--- a/test/tests.coffee
+++ b/test/tests.coffee
@@ -72,6 +72,36 @@ describe "gulp-order", ->
       stream.write newFile("b.css", path.join(cwd, "scripts/"))
       stream.end()
 
+    it "order file by last matched index", (done) ->
+      stream = order(["vendor/**/*", "vendor/**/foo/**/*"])
+
+      files = []
+      stream.on "data", files.push.bind(files)
+      stream.on "end", ->
+        expect(files.length).to.equal 8
+        relatives = files.map (file) -> file.relative
+        expect(relatives).to.equal [
+          "vendor/a.js"
+          "vendor/b.js"
+          "vendor/bar/a.js"
+          "vendor/bar/b.js"
+          "vendor/bar/foo/a.js"
+          "vendor/bar/foo/b.js"
+          "vendor/foo/a.js"
+          "vendor/foo/b.js"
+        ]
+        done()
+
+      stream.write newFile("vendor/bar/a.js")
+      stream.write newFile("vendor/bar/b.js")
+      stream.write newFile("vendor/bar/foo/a.js")
+      stream.write newFile("vendor/bar/foo/b.js")
+      stream.write newFile("vendor/foo/a.js")
+      stream.write newFile("vendor/foo/b.js")
+      stream.write newFile("vendor/a.js")
+      stream.write newFile("vendor/b.js")
+      stream.end()
+
     it "warns on relative paths in order list", ->
       expect ->
         order(['./user.js'])