To clarify, the development I mentioned above was for Wine 1.1. Prior to that, the most recent working Wine port was version 99025, which I understand could emulate a subset of APIs used in Win 3.1, Win95, and WinNT. Details about the development effort, now that I have reviewed the ports@ mailing list archive, indicate that additionally, a 1.0 port was in development in 2008.
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Occasionally, a fan of virtualbox will ask on ports@ if there is any development work ongoing. Looking through the mailing list archive, it appears that there is little interest by the ports@ community as there is a virtualbox design flaw which eliminates its use for OpenBSD on platforms without VT-x hardware. See the last post in the most recent thread:
http://marc.info/?t=126278204200002&r=1&w=2