Jaws Still Dropped: Relive The Most Unbelievable Challenge Upsets

Sometimes, the underdog comes out on top

15m ago

The Challenge is known for spawning incredible match-ups — and sometimes, the heavily stressful battles have featured some surprising results with the expected winner being defeated and sent home empty-handed. Yes, not every face-off is as easily decided as the Bananas backpack — and nail-bitters have ensued with unlikely victors emerging.

Take a look at our Challenge roundup of unbelievable upsets, below — and be sure to keep watching War of the Worlds every Wednesday at 9/8c.

1. Tyler and Bananas defeating CT and Adam during Rivals

   This last Jungle showdown was the first time Bananas and CT had met in an elimination since the aforementioned Cutthroat clash. And the Real World: Key West roomies narrowly defeated the RW: Paris alums, earning a spot in the final (and ultimately paving the way for their #1 finish).

2. Landon and Carley defeating the Fresh Meat 2 finalists field

   The Real World: Philadelphia export had already notched two Challenge wins before garnering his third with his rookie teammate. And even though Landon and Carley performed well all season (two wins and two returns from Exile), they faced extremely tough competition in the form of powerhouses Kenny and Laurel (who won five missions/one Exile throughout the season).

3. Derrick defeating Syrus during Gauntlet 2

   The objective during the 2005 match-up was to knock the other opponent out of a circle three times — and the Real World: Boston cast member was the favorite based on his height/size (a CLEAR advantage given the objective). However, Derrick completely ruled “Beach Brawl” and sent the Veteran home.

4. Camila defeating Laurel during Invasion of the Champions

   The Fresh Meat 2 recruit had never lost in this type of arena and was 9-0 when her game was on the line. But records are sometimes meant to be broken, and the Battle of the Exes champ was able to dethrone the elimination expert.

5. Devin defeating Bananas during Vendettas

   The Are You the One? contestant really wanted to face the six-time Challenge champ in The Ring — and got his way thanks to Tony’s Troika vote. Devin shined bright during “Not So Bright” (a puzzle) and sent Bananas packing.

6. Sarah versus five Gauntlet opponents

   The Queen of the Gauntlet — need we say more?