This may be a solution since this cheevo seems to be glitched:
I did it offline (internet cable unplugged) and with the cache deleted. You can delete the cache by pressing the power button on the Xbox One for 4-5 secs. I started a MyGM season with the Clippers, I let the CPU with only Jeremy Evans and played with 3 players. I won with Blake Griffin. The cheevo did not pop up, but when I got online, somehow, it popped up. I did not see it, but when I look up my achievement, there it was.
Let me know If this works for you too guys.