I have good news and bad news in terms of this achievement..
You CANNOT simulate past this, nor can you enter into the Summer League and simulate everything from there. You Must play it yourself.
You only need to play 1 Game, and it will pop at the end of the match, once you hit 'Quit'
The Fastest way to get this achievement would be to enter MyLeague and select Franchise.
Select a 14 Game Season with 1 Minute Quarters. The Other settings don't matter as you will be simming every game except for the one you play in my League.
Once you reach the off season, scroll down to the Summer League and simulate to that point. From here, play any Match and the Achievement is yours. (NOTE: You don't need to win)
EDIT: SolidTooth3160 Added: 'you can use simlive to last 30 sec and then jump in and play last 30 sec and chievo will pop.'