Jaws Still Dropped: Relive The Most Unbelievable Challenge Upsets

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


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

1. 
   
   Tyler and Bananas conquering CT and Adam while in Rivals
   
   
   
   
   
   
   This last Jungle showdown was the initial 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 conquering 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 although Landon and Carley performed well all season (two wins and two returns from Exile), they faced especially tough competition in the form of powerhouses Kenny and Laurel (who won five missions/one Exile while in the season).
   
   
   
   
   



3. 
   
   Derrick conquering Syrus while in Gauntlet 2
   
   
   
   
   
   
   the goal throughout 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 preference based on his height/size (a CLEAR advantage given the aim. Nevertheless, Derrick totally ruled "Beach Brawl" and sent the Veteran home.
   
   
   
   
   



4. 
   
   Camila conquering Laurel while in Invasion of the Champions
   
   
   
   
   
   
   The Fresh Meat 2 recruit had never lost in this kind of arena and was 9-0 as soon as her game was on the line. Nevertheless records are some days meant to be damaged, and the Battle of the Exes champ was able to dethrone the elimination expert.
   
   
   
   
   



5. 
   
   Devin conquering Bananas while in 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 throughout "Not So Bright" (a puzzle) and sent Bananas packing.
   
   
   
   
   



6. 
   
   Sarah versus five Gauntlet opponents
   
   
   
   
   
   
   The Queen of the Gauntlet -- need we mention more?