If you want to make this achievement a lot easier just take any club you want as your favorite team and a bad 1/2 star club like "Bohemian FC" from the irish league as your rival.
Go to "customise" -> "profile" -> "profile management" to change the teams.
After you've done this go to "customise" and "edit player".
Here you can put all the attributes of your favorite player/team up to 99. (For most of the skill challanges you are playing without any AI players, but in some of them you need one or more CPU Players so feel free to bump up the stats for the whole team).
If you want to make it even more easy you can set the stats of all the Rival team players to 1 (the lowest stats possible), cause in the skill games the opponent players are from the team set to rivals.
Feel free to use the comments for additional tips :)