- Season 6 finale: Larry, the Sports Hall's Butt Monkey, vs Shadow Mario/Bowser Jr.. Larry wins.
- During Season 7's Round 1, Jr. Troopa defeats Don Pinata by dropping a huge meteor on him. In their rematch in the Round 2 finale, after Jr. Troopa has evolved into a full-on Gary Stu parody, he tries the same tactic... only for the Don, previously revealed to be a former Chuckster, to catch the meteor two inches from impact and throw it back at him for the win.
Don Pianta: That's right, celestial bodies, youse don't mess wit' da Don!
- Shadoo curb-stomped his way into the final round of Season 7, becoming the second Round 3 winner. The first Round 3 winner, Anti-Guy, doesn't face good odds for Round 4. So what does the Guy do? Become a Crazy Awesome Determinator, surviving massive attacks that wiped the floor with everyone else, and did I mention catching and returning a swarm of a million hammers perfectly?!
- Anti-Guy's and Mr. L's grudge match.
- In case it hasn't been established yet, Anti-Guy is pure badass. He's the only one to win the season title twice (season champions are disqualified from future seasons).
- The Shadow Queen, having been ignored due to Kamek hijacking the battle, charges up enough power to destroy half the Sammer Kingdom dimension. (Pokey: "Forty-seven point eight percent.") It's Donkey Kong, however, who wins that fight, since he used a Crystal Coconut to become invincible just in time.
- Season 9's finale, where Waluigi shows his true abilities in a round of M.P.I.Q.. Combines with Crowning Moment of Funny.
Waluigi: ... What? You think Waluigi SAW this would happen and put questions about Waluigi near the top of the deck? You think Waluigi had no life and thought that the stupid Star would play the game that would inflate his own ego? Hah, well Waluigi would have to be the greatest in order to come up with a plan like that. OH WAIT!Roy, Larry, Kamek, Pokey: ...Kamek: .. Wow. That's... legitimately probably the smartest way anyone has ever cheated.
Awesome / Lemmy's Land
The Roy's Sports Hall section of the site is stuffed with these. A few instances (note: will most definitely spoil the fights themselves):