There's an easy way of doing this achievement which guarantees 100% win rate throughout the entire cup. This will make the achievement pretty easy and make your experience much better as well against the unfair AI.

After entering a match, if you're losing, pause and leave the game during that match. The match won't get saved, so you can just join again and restart the exact same match without any drawbacks and hopefully with a better RNG. You can repeat this forever until the RNG works in your favor and you get many goals for a win.

That's it. You'll get to the top in about 5 hours or so.