http://bugs.winehq.org/show_bug.cgi?id=25253
--- Comment #5 from Alexandre Julliard julliard@winehq.org 2010-11-24 07:15:15 CST --- (In reply to comment #4)
Wine is probably very difficult to get to work on Windows (missing POSIX APIs like the vital sendmsg used for wineserver communication, and no X11), but it should work on Windows + Cygwin + some Windows X11 server.
No, it's not going to work, particularly not for the purpose of running old 16-bit or win9x apps. Cygwin is not a virtual machine.