Unfortunately, On levels 2 and 3 it does not tell you how many you have won. I just did it the old fashion way on a piece of paper next to my computer. You need to win 10 games on each level. Once you have reached 10 you will get an message telling you that you have won the 10th game. At level 2 once you win the 10th your message will tell you to go visit the pirate, don't forget to do that because then you can play at level 3.