diff --git a/lib/path.js b/lib/path.js
index 8b08496b48e9fe..896ef7335c7307 100644
--- a/lib/path.js
+++ b/lib/path.js
@@ -58,7 +58,7 @@ function normalizeArray(parts, allowAboveRoot) {
 // Regex to split a windows path into three parts: [*, device, slash,
 // tail] windows-only
 var splitDeviceRe =
-    /^([a-zA-Z]:|[\\\/]{2}[^\\\/]+[\\\/]+[^\\\/]+)?([\\\/])?([\s\S]*?)$/;
+    /^(?:\.\.[\\\/]|\.[\\\/])*([a-zA-Z]:|[\\\/]{2}[^\\\/]+[\\\/]+[^\\\/]+)?([\\\/])?([\s\S]*?)$/;
 
 // Regex to split the tail part of the above into [*, dir, basename, ext]
 var splitTailRe =
diff --git a/test/simple/test-path-parse-format.js b/test/simple/test-path-parse-format.js
index 4f6e5af45c06e8..7a1b7883b8a78d 100644
--- a/test/simple/test-path-parse-format.js
+++ b/test/simple/test-path-parse-format.js
@@ -28,7 +28,6 @@ var winPaths = [
   'another_path\\DIR with spaces\\1\\2\\33\\index',
   '\\foo\\C:',
   'file',
-  '.\\file',
 
   // unc
   '\\\\server\\share\\file_path',
diff --git a/test/simple/test-path.js b/test/simple/test-path.js
index cdd59bcd5d93ec..11542036e8c90b 100644
--- a/test/simple/test-path.js
+++ b/test/simple/test-path.js
@@ -317,7 +317,8 @@ if (isWindows) {
        [['c:/', '//dir'], 'c:\\dir'],
        [['c:/', '//server/share'], '\\\\server\\share\\'],
        [['c:/', '//server//share'], '\\\\server\\share\\'],
-       [['c:/', '///some//dir'], 'c:\\some\\dir']
+       [['c:/', '///some//dir'], 'c:\\some\\dir'],
+       [['c:/some/random/path', '../../../../../d:/some/dir'], 'd:\\some\\dir']
       ];
 } else {
   // Posix