http://bugs.winehq.org/show_bug.cgi?id=20426
--- Comment #8 from Jörg Höhle hoehle@users.sourceforge.net 2010-03-12 10:49:36 --- If you get no music from aplaymidi -pX:Y it's not a Wine issue. Please mark this as "invalid" so it will be closed. You will be able to reopen it -- if needed -- after you get the MIDI sequencer working in UNIX.
I don't have any problems with FLuidsynth
Then please try aplaymidi with FluidSynth's port.
What happens when you invoke Timidity not in server mode, e.g. timidity -Os -iatv -s44100 -x'soundfont /usr/share/midi/xyz.sf2 order=1' You can also try other output modes. (but you'll need server mode for Wine).
Did you look into your mixer controls to see whether anything is muted? Alas, I have no idea where else to look for the problem, I'm sorry.