The Challenge: Top 10 Upsets All Time

Ammo’s almost upset against Jordan in this past week’s episode inspired me to look back at some of the greatest upsets in the history of the Challenge.

Note: If there’s one I missed, I am sorry. I made a list of 50 possible options and cut it down to these ten. I also decided not to put things like Brad vs CT or Brad vs Landon, as there is a ton of controversy among those wins.

Honorable Mentions: Cara Maria vs Aneesa (Bloodlines), Ashley winning Invasion, Veronica vs Jodi (Inferno 2), KellyAnne vs Rachel (the Island), Ty vs Abram (Exes 1)

10 Jordan beating Zach (Battle of the Exes 2)

Any man with a giant stature and long hair will receive a ton of Thor comparisons. Their elimination was a match of who can hit a girder faster with a sledgehammer. Thor was given a hammer battle against a man with one hand. The elimination between these two was not exciting in terms of the pressure and urgency that came with this elimination — more so in the impressiveness of how Jordan beat Zach. Even with his disability, Jordan showed he’s not only normal, but better. His win over Zach is the last time that he or Sarah was in danger on Exes 2. They went on to win the next two daily challenges and the final en-route to his first ever Challenge win.

9 Mike and LeRoy making the Rivals 1 final

The Rivals 1 cast was stacked from the guy perspective to put JEK vs CT. There were 3 awesome JEK teams: Kenny & Wes, Evan & Nehemiah, and Bananas & Tyler. Three pairs who combined for 10 Challenge wins (at the time), with every one of them already being Champions. Then there was CT/Adam, a duo built around CT, the most physically dominant player in Challenge history. With three spots in the final, the game became about how can JEK get all three of them to the final, and take out CT.

The little rookie team that could surprised them all and changed the plan. LeRoy was originally partnered with Adam Royer.. Adam was replaced with the small and dorky Mike Ross after a night one fight. Mike was not LeRoy’s rival, but his friend. He wasn’t a good athlete, however Mike acted as the brains of the team and never did bad enough for them to finish in last. At one point Wes/Kenny opted to face Ty/Brandon in elimination due to fear of facing Mike in a puzzle. That in itself proves Mike’s worth. Nothing is scarier to people than their weaknesses. When LeRoy climbed the rope of the final daily mission of the season faster than anyone has ever seen, he shocked the vets, forcing a CT vs Johnny/Tyler elimination. At the end of the day, they kept legendary players out of the final — that’s an upset.

8 Jill and Pete defeating Darrell and Cara Maria on Fresh Meat

Darrell was ready to get his fifth Challenge win on Fresh Meat 2. The game was made easier when he got the first overall pick in the draft (Cara Maria). Their loss was shocking as the elimination was an Exile — essentially a race. He has never been the best at daily challenges, swimming, or heights. The one thing Darrell excels in are races and obstacle courses. Darrell/Cara lost due to puzzles; it doesn’t discount the fact that Jill/Pete were the first two to eliminate one of the greatest players in Challenge history. Let alone it being the first elimination of the season. Big ups to Jill and Pete who went on to finish third in the final.

7 Jordan/Marlon defeating LeRoy/Ty on Rivals 2

This is the second appearance for Jordan and LeRoy. Throughout Rivals 2, Ty and LeRoy did not do well despite looking like a solid team on paper. When they showed up for their second elimination of the season against Jordan/Marlon, they were given the one elimination that they were built to succeed in. Hall Pass is a game that rewards speed and size, it’s a glorified Oklahoma drill with two runners and two bells at the end of the hallways., Ty and LeRoy were 200 lbs of muscle that should have bodied the combination of Marlon and Jordan. Instead, we saw Jordan utilize speed and Marlon show his football prowess in order to get a close win that put them in the final.

6 Jonna/Jasmine defeating Sarah/Katelynn on Rivals 1

Sarah Rice is one of the top seven female competitors all time. She often gloats too much about her intelligence. Her brain is what has helped her become a two time Challenge Champion. During Rivals 1, she faced Jonna/Jasmine in a puzzle elimination. Even after losing the physical portion, Jonna was still able to beat Sarah in the puzzle. This was a major win for Jonna as she cemented her place on the Challenge as a contender, and it’s the farthest that Jasmine has ever made it in a season. More than anything, the self-proclaimed puzzle expert couldn’t solve the puzzle.

5 Kim defeating Ruthie on the Duel 2

In terms of all time female competitors, Ruthie is a top ten female, and for some fans of the older generations — she is the best to them. Kim Alexander is the pretty girl from RW Hollywood who never saw herself as being very athletic, and definitely not a hands on physical player. When Ruthie called Kim in for a Duel, she thought the rookie would be an easy win.

The crowd was shocked when Kim used her size to her advantage, and took a solid 2–0 win over Ruthie. This was her biggest Challenge moment, and the last time we’d ever see Ruthie on a Challenge.

4 Cohutta defeating Wes in the Ruins

Before their match, Cohutta even said in his confessional that Wes sends people home faster than he changes his underwear. In his first three seasons, Wes had won 8 consecutive eliminations to start his career. As much as people hated him, you literally couldn’t get rid of the guy.

In the Ruins, they played Spool. It was a race of who could un-spool a ton of rope going under and over a seam. Wes always went into the Ruins with the idea of slow and steady. He quickly realized that Cohutta gained too much of a lead, and his small size gave him a major advantage. When Wes lost, he and the crowd were stunned (though they were happy).

3 Camila defeating Laurel on Invasion of the Champions

This was a true David vs Goliath match. The 5'0 Camila was able to take down the 5'11 Laurel. After the season aired, Laurel told her fans that she had an ankle injury. It may or may not be true, but injuries become bigger once you have lost. After beating Cara Maria on Invasion, Laurel took the record for most elimination wins to start a career from Wes. By being 9–0, Laurel hit a new level of dominance that nobody could touch.

The win meant a ton for Camila. After winnings Exes 1 on her third season with Johnny Bananas, she had only made 1 final (a 3rd place finish) in her following five seasons. Her status as an “elite” competitor was becoming incredibly suspect. By defeating Laurel and being the sole female champion out a group of Champions to make it to the final, the win gave Camila total validation (maybe too much).

2 Derrick defeating Syrus on Gauntlet 2

When it comes to upsets, size is usually the factor that presets people’s opinions towards “who is going to win?” In a beach wrestling to competition where you have to knock your opponent out of the ring (similar to Sumo), one would pick the 6'2 240 lb man over the 5'6 160 lb guy about 10/10 times. Not when their opponent is Derrick Kosinski. Diesel made a name for himself when he took down Syrus. People had always known that Derrick was a good competitor. Nobody knew that Derrick had THAT in him. This was the first of many moments where Derrick proved to be one of the greatest Challenge competitors ever.

1 Tina & Kenny defeating Theo & Chanda on Fresh Meat 1

During Fresh Meat 1, there were only two teams that were decently competitive with Coral & Evan til their injuries: Shane/Linette and Theo/Chanda. Before Theo became a comedian with his own Netflix special, he was killing the Challenges. He is a two time Champion who was known for being a spider monkey with no fears when it came to the Challenges. After Evelyn, Chanda was the best girl out of all the Fresh Meat. She was fast and strong, having way more upper body than any of the other girls on the show.

Meanwhile, Tina and Kenny SUCKED most of the season. For the first eight challenges, they only finished within the top half of teams twice. On top of that, they only won ONE challenge all season, the final one (the one that matters most). So when this team faced the juggernaut duo of Theo and Chanda, they were basically mince meat. Instead, Tina and Kenny killed the puzzles, found a way to work together, and clutched the end of the season to get them and Wes/Casey to the final. This was a major upset not only for them, but it also guaranteed Darrell his fourth Challenge win. The reason this win earns the number one spot is due to the plain fact that this was almost unimaginable at the time. It was the equivalent of Dario beating CT.

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Allan Aguirre

Allan Aguirre

10.6K Followers

26 years old. I blog about MTV's the Challenge and will dabble into other subjects occasionally. Follow me on Twitter for the occasional bad joke.