http://bugs.winehq.org/show_bug.cgi?id=36109
--- Comment #2 from WineBuG winebugs140@gmail.com --- (In reply to Ken Thomases from comment #1)
This looks like an issue with built-in DirectPlay (dplay). It will probably be worked around by installing native DirectPlay (e.g. "winetricks directplay").
It's basically just random happenstance as to whether built-in dplay works for a given build of Wine and/or Windows app. It's not really Mac-specific. Built-in dplay requires that a particular range of the address space be available for it to use, but there's no guarantee that the game itself or any other DLL won't use that range.
You're right "winetricks directplay" helped. I will change the name of this report to something more appropriate. Can built-in DirectPlay be fixed so that it would work out of the box?