https://bugs.winehq.org/show_bug.cgi?id=38550
--- Comment #12 from Dmitry Timoshkov dmitry@baikal.ru --- (In reply to Dmitry Timoshkov from comment #11)
(In reply to bkbk9 from comment #10)
Created attachment 56642 [details] Screenshot, wine 2.0-rc3
Screenshot of board with invisible pieces, mouse pointer turns into a hand as it hovers over a pawn on the 2nd row.
I see on your screenshot that you also have the problem with double caption (a native one from a WM and a custom one created by Chessmaster). I can't find a bugreport for this, but I have a fix for it. Once there is a bug report it will be marked as staged with a reference to appropriate patch set.
And just for the reference: what WM are you using?