http://bugs.winehq.org/show_bug.cgi?id=30210
--- Comment #7 from Grazvydas Ignotas notasas@gmail.com 2012-03-20 09:29:16 CDT --- Well that supports my guess that the game is relying on returned file order, and it can be anything on various filesystems, so you get random results.
You can create a ntfs partition and mount it or ntfs-on-a-file and mount that with loop, then install the game there to get closer to NTFS setup the game is likely expecting.