http://bugs.winehq.org/show_bug.cgi?id=20426
--- Comment #6 from Jörg Höhle hoehle@users.sourceforge.net 2010-03-12 08:33:36 --- David, please see if the newly written http://wiki.winehq.org/MIDI helps you.
client 128: 'TiMidity' [type=user]
Do you hear anything when using e.g. aplaymidi -p 128:0 foo.mid (128 is one of timidity's standard ports).
Nope I don't hear anything.
Then the problem is not with Wine and this bug report likely invalid in the Wine bug tracker. Try googling that /dev/dsp issue. OTOH, if you have ALSA, you don't need OSS' /dev/dsp. Do you have any sound fonts installed? Without them, Timidity will "play" silence only.