Easy Wins In Season Mode:

When you are in season mode fighting in a match with Ring-Out counts, store your finishing move and then get out of the ring. The person(s) fighting you should follow you. Make them fall down on the pads and when they get up, punch them and when the bend over, do your finishing move and they should still be out of the ring when the reforee gets to 10 but just to make sure, stay out until the reforee gets to 8 or 9. Then get in the ring and you will win the match.