This can be won in your first season the conference, or any other league.
When you have a cup game obviously you need to win, I found I had no problem with my crappy team winning all the games apart from the last two against Arsenal and Chelsea.
You could wait until you have a decent team with fast players that can actually kick the ball more than six foot or do what I did.
To do this early I recommend you buy some decent strikers and midfield, they don't have to cost a fortune if you buy smart, players in the high 30s to low 40s can be pretty decent.
Learns how to abuse the game, with a half decent attacking force you can score from the half way line and you can also score straight from kick off.
Everytime id get the ball I would just shoot at goal and score most times because te keepers are garbage.
The other important thing with doing this achievement is to abuse the fact if your not going to win hold the back button and close the game, reload and its like nothing happened giving you a chance to play the game again and get a move favourable result.