#17: Holly (WoO) vs. Ike (FE9/10) - Run for Political Office: I really can't say if I feel confident about Holly since she was just following her mother's orders...BUT I'm confident Ike would just quit before its started, cause he's basically "Anti-Political Authority" as far as being one goes, heck he more or less declined an offer in game!
#18: Maria (SO3) vs. Edna (XF) - Mini Golf: As if I believe Edna has the remote mental stability to put well. That's not even factoring in that Maria can probably use her powers of Alteration to CHEAT out a win.
#19: Dungeon Man (EB) vs. Necron - Mecha Combat
#20: Gilgamesh vs. Duster (Mother3) - Write a Novel: Dunno who Duster is, but I have little confidence in Gilgamesh's ability to do anything literary. Mind you, I'm sure he's a BRILLIANT actor!
#21: Kefka vs. Mewt - Treasure Hunting: Kefka actually got his hands on some nice rewards in FF6, even if it basically involved using every form of blackmail, treachery, etc. in the book...at very least, he can Slave Crown a bunch of minions into doing it for him. Mewt would be too busy whining like a little bitch.
#22: Flay Gunnar vs. Luigi Mario - Swimming Contest: As if Flay would give into someone in a competitive sport so easily! Let alone Luigi has been flanderized into being basically incompetent at anything Mario shows any sort of degree of competence in.
#23: Rafa/Malak "Special Skills" Galthanas vs. Hammer of the Mad Skillz - American Gladiator: Mad SKILLZ that Hammer has go NOWHERE in American Gladiators. At least Rafalak can wield sticks, giving them an advantage in Jousting.
#24: Frocobo vs. Joachim - Censoring Vietnamese Cable: If nothing else, Joachim would totally resort to personally entering each house and smashing every TV whenever they dare show something offensive.