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Who Won the Most Seasons of MTV’s ‘The Challenge’? Johnny Bananas and More Winners Ranked

Reality TV

Apr 4, 2024 12:27 pm·

By Alyssa Norwin

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Winning MTV’s The Challenge is no easy feat. The competition show has become quite grueling over the years, but these competitors have managed to take home multiple wins.

Seven-time champion Johnny “Bananas” Devenanzio and fan-favorite Chris “CT” Tamburello top the list of contestants with the most wins on The Challenge. Both men have won more than $1 million throughout their years of competing.

However, there are also other notable competitors who have earned three or more wins in the final – and some of the names may surprise you!

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who won the most seasons of the challenge johnny bananas

Johnny “Bananas” Devenanzio — 8

Johnny “Bananas” Devenanzio has become the face of The Challenge over the years. He’s won seven seasons of the flagship MTV show: The Island, The Ruins, Rivals, Battle of the Exes, Free Agents, Rivals III and Total Madness. Plus, he was the winner on season 1 of the spinoff Champs vs. Stars.

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who won the most seasons of the challenge ct tamburello

Chris “CT” Tamburello — 7

It took CT nearly 10 years to get his first Challenge win on Rivals II in 2013. He now has five total wins on the flagship show, as he was also the champion on Invasion of the Champions, War of the Worlds 2, Double Agents and Spies, Lies & Allies. Plus, he was victorious on seasons 1 and 2 of Champs vs. Stars.

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who won the most seaosns of the challenge darrell taylor

Darrell Taylor — 5

In his heyday, Darrell Taylor couldn’t be stopped. He won four seasons in a row in the early 2000s – The Gauntlet, The Inferno, The Inferno II and Fresh Meat – and also won season 1 of Champs vs. Pros in 2017.

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who won the most seasons of the challenge jordan wiseley

Jordan Wiseley — 4

Although Jordan Wiseley is newer to the franchise than the aforementioned legends, he’s still one of The Challenge’s G.O.A.T.s. He has three wins, taking home the championship on Battle of the Exes II, Dirty 30 and War of the Worlds 2. Plus, he won The Challenge: World Championship in 2023.

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who won the most seasons of the challenge cara maria sorbello

Cara Maria Sorbello — 3

Cara Maria Sorbello is the only solo female winner of The Challenge, a title she earned after dominating on Vendettas. Her other flagship win was on Battle of the Bloodlines, while she also took home a win on Champs vs. Pros.

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who won the most season of the challenge wes bergmann

Wes Bergmann – 3

Wes Bergmann is one of the most recognizable faces on The Challenge, but he actually only won the show two times. His victories were on The Duel and Rivals II. However, he makes the list thanks to a victory on season 3 of The Challenge: All Stars.

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who won the most seasons of the challenge veronica portillo

Veronica Portillo – 3

It’s been a while since Veronica was victorious on The Challenge. However, she did earn three wins in her early years as a competitor on Challenge 2000, The Gauntlet and The Inferno.

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who won the most seasons of the challenge kenny santucci

Kenny Santucci – 3

Kenny Santucci made it to the final in seven of his eight seasons as a Challenge competitor. He took home three wins: The Inferno 3, The Island and The Ruins.

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who won the most seasons of the challenge landon lueck

Landon Lueck – 3

Although Landon is a Challenge favorite, he’s only been on the show four times. He won three of those seasons, taking home championships during The Inferno II, The Gauntlet 2 and Fresh Meat II.

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who won the most seasons of the challenge derrick kosinski

Derrick Kosinski — 3

Derrick Kosinski is a three-time Challenge champion. He won The Inferno 3, The Island and The Ruins.

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who won the most seasons of the challenge evelyn smith

Evelyn Smith – 3

Evelyn Smith stepped away from The Challenge in 2011 but was one of the show’s most dominant competitors during her tenure. She won The Inferno 3, The Island and Rivals.

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Jamie Murray

Jamie Murray hasn’t appeared on The Challenge since 2006. However, he won all three of the seasons he competed on: Extreme Challenge, Battle of the Sexes and The Gauntlet 2.

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