With those recorded wins and losses, play the high stake CalicoJack with 'Double or Nothing' when it's multiple wins in a row and play the low stake CalicoJack when it's a loss in the next game. You'll notice that sometimes you can actually win them more than twice in a row if you're very lucky.
Get to the casino and buy some Qi coins (at least around 1,000 Qi).Make sure that your day is a very lucky day as it means there's a high frequency of winning more than two or three times in a row.Calico Jack have the same pattern of winning and losing when you restart the game and play it again on the same day.