The Wine wiki tells us how run wine with debug log 3D controller
WINEDEBUG=+wgl wine your_3d_app.exe
But crossover has a debug variable different:
CX_DEBUGMSG=+wgl /opt/cxoffice/bin/wine --bottle "WinXP" Chessmaster.exe
What the problem showed me:
err:ingl:has_opengl Failed to load libGL: /usr/lib/i386-linux-gnu/libxcb-dri3.so.0: undefined symbol: xcb_send_fd
err:ingl:has_opengl OpenGL support is disabled.
The cause is that the Ubuntu libraries 14.04 they don't play well with the libxcb that comes with Crossover. The solution is to upgrade to Crossover 13.1.3, or delete your libxcb to use Ubuntu's:
sudo rm /opt/cxoffice/lib/libxcb.so.1*