R.B.I. Baseball 21

Simply start a franchise with the lowest amount of games possible (helps reduce sim times). Go to the calendar, find the last game of the regular season (October) and sim there. Then sim through the playoffs to get to next season. Rinse and repeat until the game stops you and lets you know you've reached the end of franchise mode (it only goes 10 years) and the achievement will pop. Good luck and happy hunting!