Hi,
The Logitech controller I have, is the simpler digital Dpad which works fine.
The Logitech dual action gamepad is also supported by linux, and hence by wine,
but I don't have one of those -- what I do have, is a hacked xbox 360 controller,
which is pretty much the same thing...and it works fine as well...
Primarily speaking, the controller device must be first supported/reported to the
wine process, via the inbuilt OS drivers...ie; the native MacOSX input drivers...
this has to happen first. You don't need windows drivers - that won't work at all.
The link above -is- what most Mac people report as working, but I see it might be an
optional thing as well...(hard to say, without a Mac here to play with :)...
I'm always looking at input layer stuffs (mostly the linux side)..even right now
as it turns out, but I'm always interested in hearing about the Mac side as well,
so if you have any questions/things to report, by all means do so!
Cheers!