08 Feb 2014
The easiest method to unlock this achievement is to use a 2nd controller. Go onto the VS game mode and use a 2nd controller to start up a game. Once the battle starts, press pause on the 2nd controller and forfeit the match giving player 1 the win. Repeat this process until you are on a 5 win streak and the achievement will unlock.
Here is a short video guide I have made to follow.