diff --git a/SabreTools.Helper/Objects/Dat/DatItem.cs b/SabreTools.Helper/Objects/Dat/DatItem.cs
index a35aacbd..691611d0 100644
--- a/SabreTools.Helper/Objects/Dat/DatItem.cs
+++ b/SabreTools.Helper/Objects/Dat/DatItem.cs
@@ -756,7 +756,11 @@ namespace SabreTools.Helper
 							{
 								if ((x.Type == ItemType.Rom || x.Type == ItemType.Disk) && (y.Type == ItemType.Rom || y.Type == ItemType.Disk))
 								{
-									return nc.Compare(x.Name, y.Name);
+									if (Path.GetDirectoryName(x.Name) == Path.GetDirectoryName(y.Name))
+									{
+										return nc.Compare(Path.GetFileName(x.Name), Path.GetFileName(y.Name));
+									}
+									return nc.Compare(Path.GetDirectoryName(x.Name), Path.GetDirectoryName(y.Name));
 								}
 								else if ((x.Type == ItemType.Rom || x.Type == ItemType.Disk) && (y.Type != ItemType.Rom && y.Type != ItemType.Disk))
 								{
@@ -768,7 +772,11 @@ namespace SabreTools.Helper
 								}
 								else
 								{
-									return nc.Compare(x.Name, y.Name);
+									if (Path.GetDirectoryName(x.Name) == Path.GetDirectoryName(y.Name))
+									{
+										return nc.Compare(Path.GetFileName(x.Name), Path.GetFileName(y.Name));
+									}
+									return nc.Compare(Path.GetDirectoryName(x.Name), Path.GetDirectoryName(y.Name));
 								}
 							}
 							return nc.Compare(x.MachineName, y.MachineName);