Unlike most games where Player Match means unranked and is therefore easy to boost, in this game Player Match is Ranked. The easiest way is to get on a team of either 2 or 4 that have microphones and use them. Pair up and you should have no trouble taking towns against an unorganised team.
There is a rather simple way to boost this achievement and Old Salt, granted you have 4 controllers. (Guitars and other peripherals will work.) When you turn on all controllers, head into the Multiplayer lobby. From here, set up a Player match. You will be able to set up a player match with all four of your controllers. Set the match to be a 2 vs 2 match. You won't have to deal with any A.I. or other players, so you'll be able to win all 10 of your games easily.