You have to do this with at least one other person. Make sure that you and that one other person (or more) are in the same "club". (You can create and join clubs from the "Manage" tab in the "Pro Clubs" menu.)
After you and however many friends are all in the same club do the following:
From the main menu in FIFA 14, LB or RB to the "Play" tab, then select the "Pro Clubs" tile. LB or RB to the "Club" tab, select the "Play Match" tile.
From there have all members select a position, and then either search for a match or arrange a friendly with a group of friends in another club.
I ended up getting it by playing with only one other friend in a club. We lost our first three "random" matches because I can't play the "Any" position with any skill whatsoever - so on the fourth match we both played Forwards & let the computer control the defense, and won 2-1 on a nice pass and a nice cross to me from my buddy.
It's really not that difficult to win within a few matches just matching up randomly with some other club. It's really the easiest method to completing this achievement, because it takes fewer people and there are less complications involved.
However, if you are having difficulty with it, try forming two clubs (you'll need at least 4 friends for this method - 2 friends are in each club) - and then have the two clubs play a friendly. Let one club win, then rematch and let the other club win.
This will most likely net you the achievement - although I have no concrete verification of that fact, as of yet.
[[As of 01/09/2014, this is verified to work. Hat tip to UnlimitedStream for verifying that this method works on FIFA 14.]]
It certainly worked in FIFA 13 (although in FIFA 13 some people were saying you had to sometimes play a match between the two friendlies in order to net everyone the achievement. Again I currently have no verification that this is the case in FIFA 14. I would try playing the two friendlies back to back first, before attempting any more complicated methods).
I would, however, play each match to completion (don't quit out) if going with the second method.
Good luck!!