First off the WPS bets you can cash regardless yourself, not taxable in any form. The tri's are taxable because they are over $602.00 and at odds of 300-1. If you cash them seperately it will not matter anymore because we are in the age of computers so identical wagers can easily be matched up, where as in the past it was all paper records so a few days and different windows apart would easily solve that problem. If you cash all the trifecta's at the same time they will withhold the taxes because they total over $5,000.00, so I'd say cash you WPS tickets, then go cash your Tri's, let them withhold the %, and file for that money next year...