Increasing Your Prospects of Success. You can improve your chances of winning at rummy by controlling your hand effectively and remaining flexible. As new cards are drawn and discarded, regularly evalsaatkinguating your hand can lead to new combinations, and you can stay one step ahead of your opponents by choosing wisely which cards to keep and which to discard. At last, the key to winning at Rummy is knowing when to give up and how to remain composed under duress. You'll undoubtedly experience some suspense and anxiety as the game goes on as you consider your options for drawing & discarding cards.