Event 18: Babysitting
The most criminally underpaid and probably illegal practice in the western world, giving some random neighbor $20 so a couple can run away from their children for a few hours. For maximum results, contestants will be babysitting 3 children, aged 2, 4, and 5. Success is judged on causing the least psychological, physical, and property damage during the event.
Samus Aran is an intergalactic bounty hunter and stuff.
The Genie has semi-phenomenal, nearly-cosmic powers.
Event 19: The Statue
A favorite of parents of small children, the statue game involves being completely still for as long as possible. Seems simple enough.
Ilyana the perpetually hungry will do about anything for a meal. usually this involves manipulation and exploiting others, but maybe she can hold still for a long time on promise of dinner. Or maybe she'll faint away from hunger after 15 minutes.
Umi is a lovesick seagirl. Probably completely crazy. Cthulhu man.
Event 20: Yo Momma Fight
The gauntlet is thrown. Your rival stands before you. The only path: insult their mothers until they can't fire back!
Visser Three is the primary foe of the Animorphs. Owning to controlling an Andalite, he can shapeshift into any animal he's absorbed the DNA of. I'm not sure how that helps in this contest, and I'm not sure Yerks have parents as mammals understand them, but so it is.
Lilianne Valendorf is an up and coming alchemist at Al Revis. Her extra-curricular is legendary. Her expertise in insults is mocking someone's general intelligence and background, but she can probably expand her repertoire.
Event 21: 'Dwarf' Tossing
A perennial favorite, the dwarf toss! However, owing to suits brought forward by various associations for little people, tossing actual dwarves is not permitted this year. Instead, contestants will be divided into teams of two, and among them decide which will be tossed and which will be throwing.
Yukari Yakumo, denizen of Gensokyo. Zelos Wilder, Chosen of Tetha'ala. Yukari has vast, vaguely defined powers, but it's uncertain if there's a correct application for this event, and those powers don't to my knowledge apply to physical strength. Zelos would never toss a cute girl though, so this team may be at an impasse.
Yuri Lowell, errant vagabond. Athena Cykes, of the Wright Anything Agency. Athena's prone to physical comedy, and Yuri's a pretty strong guy, so while they may not do WELL they'll at least complete the event.
Event 22: Bullfighting
Olé! Competitors will be judged on putting on the best show will still successfully slaying the bull and not being seriously injured.
Mr. Clean is magical and can certainly make things look good. Deadliness is another matter.
Miriel is not known for her physical durability, but I'm sure she'll study the matter thoroughly before coming to the arena.
Event 23: Thumb Wrestling
One two three war I declare thumb war!
The Nostalgia Critic most definitely has thumbs.
Princess Buttercup ALSO has thumbs.
Event 24: Kidnapping Princess Peach
Being as Bowser is still being retrieved from the wreckage of a preposterous Jenga tower, the monthly quota on Princess Peach kidnappings is way down, and the Mushroom Kingdom economy has taken a sharp downturn. As a result, our contestants must stand in for Bowser, and successfully kidnap Peach, take her through at least 8 unique castle settings, and set up a final encounter for Mario's rescue attempt. In the event both contestants are successful, they will be judged on their ability to be evil.
Squidward will almost certainly get a kick out of playing Bowser. Whether he's competent enough to do it...
Domon Kasshu is not in his element here. Much better at saving princesses. Still, he probably COULD do it, even if he wouldn't, which may well put him ahead of the competition.
Short Form
Babysitting: Samus Aran (Metroid Series) vs Genie (Aladdin)
The Statue: Ilyana (Fire Emblem Series) vs Umi (Cthulhu Saves the World)
Yo Momma Fight: Visser Three (Animorphs) vs Lilianne Valendorf (Mana Khemia 2: Fall of Alchemy)
Dwarf Tossing: Yukari Yakumo (Touhou Series) and Zelos Wilder (Tales of Symphonia) vs Yuri Lowell (Tales of Vesperia) and Athena Cykes (Phoenix Wright Ace Attorney: Dual Destinies)
Bullfighting: Mr. Clean (Mascot) vs Miriel (Fire Emblem: Awakening)
Thumb Wrestling: Nostalgia Critic (That Guy with the Glasses) vs Princess Buttercup (The Princess Bride)
Kidnap Princess Peach: Squidward (Spongebob Squarepants) vs Domon Kasshu (Mobile Fighter G Gundam)