In order to get this achievement you must obtain 50 wins in the road to glory mode. This can be located in the MY PLAYER menu. After this it will ask you to create 2 characters, 1 male and 1 female for both your online career and offline career mode. Then choose Road To Glory mode.
You have 2 options, featured match or tonights match. I can confirm BOTH count and you can mix it up if one day its a long match like a ladder or iron man match.
This is extremely easy to do boosting but you must do the following...
Player 1 searches for a game, once the the pop up shows looking for opponent 0/1 then tell Player 2 to search. You should instantly get matched as there is literally no one playing this game online. Rinse and Repeat. For some reason if you search at the same time it wont find your partner which was pretty strange but the above worked with no problems.
Sometimes you may have to get the other player to search first and do it that way as sometimes the looking for opponent will get stuck. On the very rare occasion you may come across a random person but this was very few and far between when me and my buddy were boosting it.