diff --git a/src/Microsoft.AspNet.Mvc.TagHelpers/Internal/GlobbingUrlBuilder.cs b/src/Microsoft.AspNet.Mvc.TagHelpers/Internal/GlobbingUrlBuilder.cs
index ac8c1bb4d1..6120814dac 100644
--- a/src/Microsoft.AspNet.Mvc.TagHelpers/Internal/GlobbingUrlBuilder.cs
+++ b/src/Microsoft.AspNet.Mvc.TagHelpers/Internal/GlobbingUrlBuilder.cs
@@ -153,14 +153,22 @@ public int Compare(string x, string y)
                 var xExtIndex = x.LastIndexOf('.');
                 var yExtIndex = y.LastIndexOf('.');
 
-                var xNoExt = x.Substring(0, xExtIndex);
-                var yNoExt = y.Substring(0, yExtIndex);
+                // Ensure extension index is in the last segment, i.e. in the file name
+                var xSlashIndex = x.LastIndexOf('/');
+                var ySlashIndex = y.LastIndexOf('/');
+                xExtIndex = xExtIndex > xSlashIndex ? xExtIndex : -1;
+                yExtIndex = yExtIndex > ySlashIndex ? yExtIndex : -1;
+
+                // Get paths without their extensions, if they have one
+                var xNoExt = xExtIndex >= 0 ? x.Substring(0, xExtIndex) : x;
+                var yNoExt = yExtIndex >= 0 ? y.Substring(0, yExtIndex) : y;
 
                 if (xNoExt.Equals(yNoExt))
                 {
                     // Only extension differs so just compare the extension
-                    var xExt = x.Substring(xExtIndex);
-                    var yExt = y.Substring(yExtIndex);
+                    var xExt = xExtIndex >= 0 ? x.Substring(xExtIndex) : string.Empty;
+                    var yExt = yExtIndex >= 0 ? y.Substring(yExtIndex) : string.Empty;
+
                     return xExt.CompareTo(yExt);
                 }
 
diff --git a/test/Microsoft.AspNet.Mvc.TagHelpers.Test/Internal/GlobbingUrlBuilderTest.cs b/test/Microsoft.AspNet.Mvc.TagHelpers.Test/Internal/GlobbingUrlBuilderTest.cs
index 3738eb809b..676f6a5261 100644
--- a/test/Microsoft.AspNet.Mvc.TagHelpers.Test/Internal/GlobbingUrlBuilderTest.cs
+++ b/test/Microsoft.AspNet.Mvc.TagHelpers.Test/Internal/GlobbingUrlBuilderTest.cs
@@ -163,6 +163,44 @@ public static TheoryData OrdersGlobbedMatchResultsCorrectly_Data
                             "/A/site11.css", "/A/site2.css",
                             "/B/site11.css", "/B/site2.css"
                         }
+                    },
+                    {
+                        /* staticUrl */ "/site.css",
+                        /* dirStructure */ new FileNode(null, new [] {
+                            new FileNode("B", new [] {
+                                new FileNode("site"),
+                                new FileNode("site.css")
+                            }),
+                            new FileNode("A", new [] {
+                                new FileNode("site.css"),
+                                new FileNode("site")
+                            })
+                        }),
+                        /* expectedPaths */ new []
+                        {
+                            "/site.css",
+                            "/A/site", "/A/site.css",
+                            "/B/site", "/B/site.css"
+                        }
+                    },
+                    {
+                        /* staticUrl */ "/site.css",
+                        /* dirStructure */ new FileNode(null, new [] {
+                            new FileNode("B.B", new [] {
+                                new FileNode("site"),
+                                new FileNode("site.css")
+                            }),
+                            new FileNode("A.A", new [] {
+                                new FileNode("site.css"),
+                                new FileNode("site")
+                            })
+                        }),
+                        /* expectedPaths */ new []
+                        {
+                            "/site.css",
+                            "/A.A/site", "/A.A/site.css",
+                            "/B.B/site", "/B.B/site.css"
+                        }
                     }
                 };
             }