What makes this elimination upset so huge is that the elimination itself was a puzzle. Sarah was very confident that they would crush Jonna and Jasmine, especially if it were Sarah’s forte (puzzles). The duos played in a game where one player is taken away ahead of time and locked in a coffin, buried under a pile of hay. The other partner must dig through the hay to find their partner, and once found, they then solve a puzzle.

Jonna was able to solve the puzzle faster than Sarah, and they lived another day in a game built against them. It was the peak of Jonna and Jasmine’s Challenge career; they never accomplished anything more significant than this, which is a bit sad, but beating Sarah is a huge deal. Sarah Rice is a career 6–2 in elimination. She never lost another elimination after this season, made three finals, won two seasons, and to this day, her only other loss was to Laurel/Kenny. They took down a Challenge legend in their rookie seasons.

6 Nate & Christina defeating Cory & Ashley on Rivals 3

Seeing Cory get embarrassed in something isn’t too shocking of an outcome, but at this point in time, MTV was building Cory up as a significant player. Cory finished 2nd place on his rookie season, and he and Ashley were looking like a formidable pair on Rivals 3. When they faced lay-ups, Nate and Christina, they expected to win with ease. The elimination was one player pushed a giant lever to pull a player hanging on a bar attached to a rope. As they push more, the line extends, and the amount of tension increases. Cory and Ashley figured they would win this elimination with ease because they were much bigger and stronger than Nate and Christina. Unfortunately, they played the elimination with the wrong strategy.

In this type of elimination, the key to holding the bar is relaxing your muscles as much as possible. The tighter you hold, the more the tension cramps your muscles. Sarah Rice gave Christina this insight before the elimination as she played the “O Ring” elimination on the Ruins and almost lost trying to pull too hard. What’s crazy is that when Christina wins Round 1, when she finally releases, she gets shot into the nether, displaying that Cory was actually pushing the turnstile quite a bit.

Nate and Christina never got cast again, while Ashley would go on to become a 2x Champion and is one of the most prominent figures in Challenge history. Meanwhile, Cory continued to fail upwards into multiple seasons and franchises.

5 Derrick defeating Syrus on the Gauntlet 2

Derrick has pulled off a lot of big wins in his Challenge career. However, the one that truly established him as a monster physical competitor was when Derrick took out Syrus in Beach Brawl. A game that was essentially a sumo battle/wrestling hybrid. Derrick took advantage of his ability to get lower than Syrus and had ridiculous in-ring awareness of when to push Syrus out. People see this win from Derrick and think, “oh wow, he can go toe to toe physically with someone much bigger.” From a pure size perspective, Derrick can’t, but he understands the angles and outsmarts Syrus like crazy. Derrick isn’t book-smart, but he has the mind of a fighter/wrestler. Honestly, in another world, if Derrick gets born like 8–10 years later, he probably becomes a pretty good pro-MMA fighter.

If you watch his elimination with Joss 14 years later, Derrick has crazy spacial awareness. In that elimination, a ring out creates a restart; and every time he almost loses, Derrick gets the reset immediately. It’s intuitive to him.

4 Tina and Kenny defeating Theo and Chanda on Fresh Meat 1