5th Grader Game Time

One thing to add to monkey540's guide is that if the achievement does not click right away what worked for me was going back and replaying the games and making sure i completed it by winning the maximum amount of money possible. For example in three and out win a million and in home room also win a million. The achievement clicked for me after I played battle of wits again and got my streak counter all the way to the top to earn the win. Showroom showdown is the only game where there is not a "maximum" amount of money you can win, just make sure its more than your opponent. Hope this helps!

For this one, you must win one of each of these game types online.

Homeroom
Showroom Showdown
Three and Out
Battle of Wits

for all the games you MUST score points, 1000 points is good enough. No ties allowed except in Homeroom, I think if both players get the 1000000 it counts as a win.