Ok you can get this achievement:
Here is how to do this, you will need a friend to do this:
go to Online league
invite your friend
when he accepts your invite, go into the league. on the league option screen:
Number of teams (2 teams)
Season Lenght (1 game per team)
Playoffs (yes 2 teams)
then start league.
once league starts. go to schedule section and simulate the game on the list.
then once you have done this, simulate again, i got this on first try, i won the 2nd game and achieved the achievement.
edit: it seems that this achievement is rather glitchy, it unlocked for me, but it didnt unlock for my friend who i tried it with... so it seems they have fixed it, but it still has issues.