I'm taking a shot in the dark hoping someone here has figured this out, because they haven't figured it out at winehq, which I know is the more appropriate forum to ask. But,no one knows (that I know of), so here goes:
Do you know how to get the wacom pen pressure to work in Adobe Photoshop CS5 using wacom tablet? It works fine in MyPaint, Gimp, Pencil etc. So I know this is a wine issue with the wacom pressure settings.
I can provide any information you feel is helpful in solving this, just ask.