I'm by no means an expert in this, but from the cups log it looks to me like cups thinks it printed the job successfully. What exactly happens with your printer when you try to print--does anything come out at all? Does the light blink to indicate it's receiving data? There is a cups backend called cups-pdf that prints to a PDF file. I've used it with Word 2003, so it definitely works Wine. That could be a workaround for you.
