The Challenge: Total Madness

• Battle Lines: Played in male and female heats, contestants must pull a barrel of medical supplies across a field, solving a math problem and puzzle along the way. At intervals, players who fall behind are eliminated from the challenge by having their barrel run over by a tank. The first player in each heat to reach the end of the field wins.
  • Winners: Jenny & Rogan
• Airdrop Extraction: Played in nine teams of three, teams must transfer 15 military crates from one missile launch platform to another, one mile apart. The first three teams to finish advance to Round Two. In Round Two, teams board a helicopter and must drop nine military crates from the helicopter, aiming to hit the missile launch platform. The team with the most hits wins.
  • Winners: Cory, Dee & Swaggy C
• Decode and Detonate: Each player begins at a puzzle board with a code. They must race to two separate puzzle keys to obtain the key to their code before returning to solve the code. Once the puzzle is solved, players race to a detonator and blow up a truck. The first two players to detonate a truck, wins.
  • Winners: Bayleigh & CT
• Cold War: Played in five teams of five, three players from each team must collect puzzle pieces from the bottom of a pool before solving the puzzle. Meanwhile, two players from an opposing team break an ice block to send ice into the pool, making the water less tolerable for those collecting pieces. The team with the fastest time wins.
  • Winners: Aneesa, Bananas, Bear, Big T & Kaycee
• Bomb Squad: Played in six teams of four, each team member has a specific role. The first player must ride in a stunt car and look for hidden numbers to form a math equation, communicating this to a second player via radio. The second player solves the equation and runs the answer to the third player, who decodes the puzzle and selects three corresponding rods. The third player run the rods to the fourth player, who places the rods in a detonator. If the rods are correct, the bomb detonates. The team with the fastest time wins.
  • Winners: Jenny, Josh, Kaycee & Swaggy C
• Fast & Furious: Played in male/female pairs, each pair is hooked to a moving semi-truck and tethered together. Two pairs play at a time, on opposite sides of the truck. They must collect ten magnetic puzzle pieces from the side of the truck, before returning to their puzzle board at the top and solving the puzzle. The pair with the fastest time wins. Inspired by scenes from F9.
  • Winners: Jordan & Nany
• Decontamination: Each player races through a room of foam towards a window, while wearing PPE, where a series of flashing lights are shown. They must memorize the series before returning to the entrance and replicating the sequence, by placing colored disks around a pole. The male and female with the fastest time wins.
  • Winners: Mattie & Wes
• Tunnel Rats: Played in three teams of five and one team of four, with two teams playing at once. One at a time, team members slide down a chute into a tunnel and swim to retrieve puzzle pieces. Once all five puzzle pieces are collected, they must run back to the entrance and solve the puzzle. The team with the fastest time wins.
  • Winners: Bayleigh, Cory, Dee, Nany & Wes
• Throne Off: Played in male and female heats, players begin holding onto a missile above water. One at a time, they are asked a multiple-choice trivia question. If they answer correctly, they can assign a strike to another player while answering incorrectly self-incurs a strike. Players are eliminated if they receive two strikes, or fall after letting go of the missile. The last male and female standing win. Additionally, both winners received a $5000 cash prize, announced at the conclusion of the challenge .
  • Winners: Dee & Wes
• Flag Down: Two players of the same gender begin strapped on each side of a tank, with four players competing at once. As the tank drives through a course, they must collect as many flags as possible, where red flags are worth one point and white flags are worth ten points. The male and female with the most points win. At the conclusion of the challenge, it was announced that players who had worked together during the challenge were disqualified.
  • Winners: Josh & Melissa
  • Disqualified: Fessy, Jenny, Kyle, Nany, Nelson & Rogan
• Tanks-A-Lot: Played in five teams of three, teams transfer junk from a junkyard across a field and deposit it into a bin. At the end of an unspecified time period, the two teams that transfer the most weight advance to Round Two. In Round Two, each team member must pull a heavy sled across the field. The first team to pull all three sleds to the finish line wins.
  • Winners: Bayleigh, Dee & Fessy
• Bloc'd In: Played in two teams of seven. Similar to a slide puzzle, teams push a series of black cars forwards or backwards in order to release a red car. Once released, teams must push the red car past the finish line. The team with the fastest time wins.
  • Winners: Aneesa, Bananas, Cory, Jenny, Josh, Nany & Rogan
• Running Out of Time: Players must run to collect heavy material before returning to place it into an opponent's drum. After an unspecified time period, a horn sounds, indicating that players have five minutes to return and pick up their drum. Players who do not return in time are disqualified. The male and female to hold their drum up the longest wins.
  • Winners: Fessy & Jenny
  • Disqualified: Aneesa, Kyle & Nelson
• Crash Course: Similar to bowling, one player begins in a stunt car and must crash the car into piles of barrels which other contestants are standing on. The male and female who knock down the most barrels win. In the event of a tie, the winner is determined by how far their barrels travelled.
  • Winners: Bananas & Kaycee

• Air Strike: Players begin hanging on to a bar above ground. Between them is a clear wall which they can kick to attempt to make their opponent drop from the bar. The first player to make their opponent release the bar twice wins.
  • Played by: Asaf vs. Jay
• Flip the Switch: Players begin on opposite sides of a hallway, each with ten barrels attached to poles. They must flip all ten barrels over the rail so that it lands on their opponent's side. The first player to flip all ten barrels and flip the switch at the end wins.
  • Played by: Jenn vs. Jenny
• Take Shelter: Players have 20 minutes to barricade the entrance to a bunker using provided materials. After those 20 minutes are up, players must attempt to break into their opponent's bunker, fully opening the door. The first player to break into the bunker and switch on the light wins.
  • Played by: Jay vs. CT
• Code Breaker: Players spin five wheels and must break hanging ceramic pots to find the corresponding tiles to the symbols that they spun, using a large die as a stepladder. After finding all five tiles, they flip the tiles over to reveal the names of five previous seasons of The Challenge. The first player to correctly place the seasons in chronological order wins.
  • Played by: Ashley vs. Dee
• Fire Ball: Similar to "Balls In" from The Inferno II, except this time the ball is on fire. Each player is given three chances per round to get a ball inside a barrel, located in the middle of a large circle. If a player is either knocked out of or steps out of the ring, or if the ball is knocked out of the ring, their ball is considered "dead". Players alternate between offense and defense in each round. The player who scores three points wins, with each ball being worth a point.
  • Played by: Jay vs. Rogan
• Dust to Dust: Players must take bricks up a ramp and smash them through a grate so that the debris falls into a wheelbarrow underneath. They then use the wheelbarrow to transfer the debris into a container and continue until enough debris is collected to reach a designated height level. The first player to reach the designated height wins.
  • Played by: Jenna vs. Tori
• Pole Wrestle: Originally from The Duel. Players are placed at the center of a circle and place both hands on a metal pole. The first contestant to wrestle the pole out of their opponent's hands twice wins.
  • Played by: Fessy vs. Jordan, Nelson vs. Bear
• Bombs Away: Players begin in a bin with one hundred bombs. They must unload all one hundred bombs from the bin before detonating a smoke bomb. The first player to ignite their smoke bomb wins.
  • Played by: Kaycee vs. Kailah, Aneesa vs. Jenna
• Charge the Wall: Players must break through boxes of a wall to climb the wall and find batteries inside the boxes. The first player to find all three batteries wins.
  • Played by: Bananas vs. Wes
• Tunnel Vision: Players begin at one end of a locked tunnel filled with dirt. They must dig through the dirt to reach the other end to escape. The first player to escape their tunnel and ring the bell, wins.
  • Played by: Dee vs. Mattie
• Launch Button: Players begin harnessed to opposite sides of a container. Each side has twenty buttons that correspond to a light. They must swing and press all twenty buttons to switch on every light. However, pressing a button twice turns the light off. The first player to light up all twenty lights wins.
  • Played by: Cory vs. Swaggy C
• Off With Your Heads: Similar to "Striptease" from Dirty 30. Players wear a jumpsuit with five mini red skulls placed on various parts of the body. The first player to pull off all five skulls from their opponent's jumpsuit and place them on their podium, wins.
  • Played by: Melissa vs. Nany
• Knots of War: Similar to "Knot So Fast" from Battle of the Seasons (2012) players have 15 minutes to create as many knots as they can using rope within a car. After those 15 minutes are up, players must untie their opponent's knots. The first player to untie all of their opponent's knots and bring the rope outside of the circle, wins.
  • Played by: Aneesa vs. Bayleigh, Josh vs. Kyle
• Hall Brawl: Originally from Battle of the Seasons (2012). Players must run through a narrow hallway, past their opponent and ring a bell. The player who rings the bell first twice, wins.
  • Played by: Dee vs. Jenny, Nelson vs. Rogan

Checkpoint One: Players must strap on skis and ski over towards a pile of logs. They can take up to three logs before skiing across a valley towards a skull monument to deposit the logs. Once a player has collected twelve logs, they must ignite a fuse and light up their monument before proceeding to the end of the checkpoint. Unbeknownst to the players, the first male and female to finish the checkpoint form the final Tribunal of the season, for an Instant Elimination.

• Tribunal: Cory & Jenny

The Journey: All nine players must traverse a via ferrata together, to reach a compound at the top of a mountain, crossing a tightrope along the way. Once they reach the compound, players not in the Tribunal must select one male and one female to participate in an Instant Elimination. The Tribunal also selects one male and one female for the Instant Elimination.

Instant Elimination - Knockout: Players start at opposite ends of a ring and must race to ring a hanging bell in the middle before their opponent. The player to ring the bell first twice, wins.

• Played By: Bananas vs. Rogan
• Winners: Bananas & Kaycee
• Eliminated: Melissa[lower-alpha 4] (4th place - Quit), Rogan (5th place)

Overnight Stage: Both Tribunal members and both winners of the Instant Elimination are rewarded with a warm room to sleep inside of the compound for the night. The remaining three players must spend six hours outside by a fire before being allowed inside of the compound.

• Eliminated: Bayleigh[lower-alpha 3] (3rd place - Quit)

Final Push: Players follow a trail until they reach the glacier where the finish line is set up. Tribunal members have a two-minute headstart and the Instant Elimination winners have a one-minute headstart. Along the way, there are a series of math operations, the solution of which forms the combination to unlock a skull, that they must smash before proceeding. The first male and female to cross the finish line are declared the winners of Total Madness and receive $500,000 each.

• Winners: Bananas & Jenny
• Runners-Up: Kaycee & Kyle
• Third Place: Cory
• Fourth Place: Fessy

Competition

  The contestant finished the final challenge and won.

  The contestant finished the final challenge and lost.

  The contestant did not finish the final challenge.

  The contestant won the challenge and was part of the tribunal.

  The contestant did not win the challenge, but was part of the tribunal.

  The contestant was not selected for the Purgatory.

  The contestant was nominated by the tribunal for interrogation, but was not selected for the Purgatory.

  The contestant won the Purgatory and earned a Red Skull.

  The contestant was part of the tribunal, volunteered for the Purgatory, won and earned a Red Skull.

  The contestant lost the Purgatory and was eliminated.

  The contestant was part of the tribunal, volunteered for the Purgatory, lost and was eliminated.

  The contestant was removed from the competition due to injury/illness.

  The contestant withdrew from the competition.

• Episode 1: "Battle Lines"
• Episode 3: "Decode and Detonate"
• Episode 8: "Decontamination"
• Episode 10: "Throne Off"
• Episode 11: "Flag Down"
• Episode 14: "Running Out of Time"
• Episode 15: "Crash Course"

The Reunion special aired on July 22, 2020, and was hosted by former NFL player Vernon Davis. Due to the COVID-19 pandemic, it was conducted by way of a Zoom chat. It was watched by 0.78 million viewers.[20] A behind-the-scenes special, also hosted by Davis, aired on July 29, 2020, and was watched by 0.49 million viewers.[21]

Challenge in bold indicates that the contestant was a finalist on The Challenge.