1) the act of crossing the basketball from one hand to other while dribbling. a technique designed to confuse one's opponent
2) to outwit someone through skills
1) The player crossed up his opponent and then used his body as a ladder to dunk the ball in the basket.
2) she was an inferior trader but through her tenacity Susan was able to cross-up the competition and get the trade done
After your boss has gone for the day, you take a shit in his top desk draw, lock it and taking away the key.
Than you proceed to write him an email letting him know you are resigning and today is your last day.
John resigned today but left his boss a Desk Deuce as great appreciation for the leering experience.