Not too difficult to do with a little determination.
Pick a strong team with high-class attacking players and wait for an early domestic cup game against a weak opponent in the lower tier leagues.
Ahead of the game, promote youngsters to your senior squad, preferably ones who suck. Add all these players to your starting lineup and put your strong attacking players on the bench. Arrange the weirdest formation you could think of (I did a 1-5-4 formation) and place your weak youngsters in positions they are uncomfortable playing.
Start the game and hopefully you will concede some goals. If not, just restart and tweak your tactics. In my game, after a few attempts, the score was 2-5 after the first half. During half-time, switch back to a proper formation and sub in the strong attacking players and pray for the best. In the end I won 7-6.
I would also like to add that, if the game ends in a tie and you manage to win after overtime and/or penalties, the achievement unlocks as well.