I had issues with this achievement unlocking. I won the Rookie/Sophmore game in one sitting. Then the next day I beat the 3-Point challenge, Slam Dunk, and All Star game in another sitting unlocking all the achievements, but not this achievement.
I played another Rookie/Sophmore game again because I played the other three in one sitting. So the key is to beat all four in one sitting.
PLAY ALL FOUR IN ONE SITTING