Switchball

Make sure to hit the Y button on the multiplayer main menu to turn this into a ranked match before you start. Only ranked wins count. Quitting out of the session will not give the other player a win. The first multiplayer race level takes roughly a minute and ten seconds to one minute and thirty seconds per race once you are both familiar with the track. The player who is not going for the achievement should still head for the finish line to avoid waiting for a thirty second timeout after the first player crosses. All said it takes about seven minutes per player to get five wins.