diff --git a/src/System.Runtime.Extensions/tests/System/IO/Path.GetRelativePath.cs b/src/System.Runtime.Extensions/tests/System/IO/Path.GetRelativePath.cs
index 36a03d6bfc9f..3f48bfd9ccb5 100644
--- a/src/System.Runtime.Extensions/tests/System/IO/Path.GetRelativePath.cs
+++ b/src/System.Runtime.Extensions/tests/System/IO/Path.GetRelativePath.cs
@@ -17,12 +17,26 @@ public static class GetRelativePathTests
         [InlineData(@"C:\", @"C:\b", @"b")]
         [InlineData(@"C:\a", @"C:\b", @"..\b")]
         [InlineData(@"C:\a", @"C:\b\", @"..\b\")]
+        [InlineData(@"C:\a\b", @"C:\a", @"..")]
+        [InlineData(@"C:\a\b", @"C:\a\", @"..")]
+        [InlineData(@"C:\a\b\", @"C:\a", @"..")]
+        [InlineData(@"C:\a\b\", @"C:\a\", @"..")]
+        [InlineData(@"C:\a\b\c", @"C:\a\b", @"..")]
+        [InlineData(@"C:\a\b\c", @"C:\a\b\", @"..")]
+        [InlineData(@"C:\a\b\c", @"C:\a", @"..\..")]
+        [InlineData(@"C:\a\b\c", @"C:\a\", @"..\..")]
+        [InlineData(@"C:\a\b\c\", @"C:\a\b", @"..")]
+        [InlineData(@"C:\a\b\c\", @"C:\a\b\", @"..")]
+        [InlineData(@"C:\a\b\c\", @"C:\a", @"..\..")]
+        [InlineData(@"C:\a\b\c\", @"C:\a\", @"..\..")]
         [InlineData(@"C:\a\", @"C:\b", @"..\b")]
         [InlineData(@"C:\a", @"C:\a\b", @"b")]
         [InlineData(@"C:\a", @"C:\A\b", @"b")]
         [InlineData(@"C:\a", @"C:\b\c", @"..\b\c")]
         [InlineData(@"C:\a\", @"C:\a\b", @"b")]
+        [InlineData(@"C:\", @"D:\", @"D:\")]
         [InlineData(@"C:\", @"D:\b", @"D:\b")]
+        [InlineData(@"C:\", @"D:\b\", @"D:\b\")]
         [InlineData(@"C:\a", @"D:\b", @"D:\b")]
         [InlineData(@"C:\a\", @"D:\b", @"D:\b")]
         [InlineData(@"C:\ab", @"C:\a", @"..\a")]