This achievement is really simple and shouldn't take more than the length of a normal singles match. If you are new to the 2K games, you can always lower the difficulty as this and any other achievement based on the Payback system can be done on any setting.
Every wrestler has a default payback assigned to them, but at the character select screen you can edit the Payback your wrestler has, so choose your favorite wrestler and change their Payback to Auto-Reversal. During the match, your Payback meter fills as you take damage, so let your opponent beat you up and use your Payback as soon as it's ready. You can activate it by pressing LB & RB at the same time and then to use the auto-reversal just hold R trigger before your opponent tries to strike you or grapple you.
Obviously letting your opponent beat you up can cause you to lose the match before you activate your Payback three times, so I would suggest using it right before your opponent tries to use their signature or finisher.