The easiest way to "win" this achievement is to make use of the lobby rooms which are always unoccupied with a friend.
For instance select from menu's Xbox LIVE> Community> Lobby then select the 'Geography" blade. While in a party with your friend, who you'll boost with, decide on a specific lobby "My Country #1" e.g.
Have one player start a session, select "Ranked Shootout" and invite the other, now you'll be playing a ranked game with a friend and able to boost for the achievement.
The player going for the achievement will select a OHL, WHL or QMJHL team and have your partner let you score on them to win. Also can be linked with the :
if you want to string together another four wins on top to total five.
Please vote positive if this helped you out :)