The Gauntlet II marked T. J. Lavin's first time presenting the series, regularly hosting the program from this season forward. Prior seasons only used temporary hosts. The season is the second in the Gauntlet series, with the original Gauntlet airing in 2003–2004 and The Gauntlet III following in 2008.
The Gauntlet II aired in late 2005 and into 2006 with 32 contestants and took place in Trinidad and Tobago.
The teams were designated Veterans and Rookies, based on the number of prior Challenge seasons on which each cast member had competed. Those on the Veterans team had been on at least two prior seasons, and those on the Rookies team had been on fewer than two seasons. For this season, a male and female captain were determined at the beginning of the season. After each team challenge, the losing team captain was sent to the "Gauntlet", where they would face an opponent of the same sex and same team who was voted into the Gauntlet by the respective team. Gauntlets alternated between "Male Gauntlets" and "Female Gauntlets".
- For this challenge, a male and female captain were determined at the beginning of the show based on physical prowess, although some chose to use rock-paper-scissors to decide.
- Jo made her first appearance in a Challenge, marking her first return to MTV in eleven years, and quickly caused controversy in the first episode. She called the police to escort her out and leave the show after she found being in the house with 31 other cast members intolerable.
- Derrick blew up at his team for choosing a secret ballot method for voting into the Gauntlet rather than openly stating their votes.
- After the Rookies lost the second challenge, Kina picked Cameran for the Gauntlet. Cameran voluntarily lost, feeling Kina would be a better captain than she would. Many of the Veterans were astounded at this, especially after Derrick and Adam L. fought so hard in the previous Gauntlet. This led to an argument between Cara and Aneesa, with Timmy mimicking Aneesa's rant behind her.
- Danny harbored intense hatred towards his former Road Rules cast member Jodi, due to his belief that she manipulated the cast into voting him off. After being called out in the "Moving Pyramid" challenge, Danny lashed out at Jodi, which then led to Alton pulling Danny into the Gauntlet. He went on another tirade, claiming he would easily defeat Alton in the Gauntlet, but was beaten in a humiliating fashion.
- Jisela volunteered to go into the Gauntlet and lost to Ruthie. Host T.J. Lavin commented that Jisela pretty much quit the game.
- In a Veterans team meeting Ace took fault for the failure during a mission and volunteered to go to the Gauntlet. He and Derrick went head-to-head in a wrestling beach brawl. Derrick stayed low and powered his way through Ace to keep his role at Veteran captain.
- When Beth reveals to Robin that Jodi had told her that Mark, who Robin was seeing at the time, said he was in love with her, she confronted Mark, who became so angry with Robin that he punched the bus and walked home.
- While strategizing for a mission in which a team member had to pull other team members around a track in a large rickshaw, Beth decided that she should be the one teammate who would sit out, due to her being the biggest woman on the team (the veterans had to sit one man and one woman out due to having more players than the rookies). Montana, along with several other members, believed that Beth was manipulating Ruthie so that she would get immunity from the Gauntlet. The team sided with Montana and let her sit out. Beth performed well in the mission, but the team lost. Beth was voted into the Gauntlet against Ruthie, but stunned the team by beating her at the Reverse Tug-of-War, thus becoming the new female team captain.
- While her team hoped she would be eliminated as soon as possible, Beth defeated both Ruthie and Montana in "Reverse Tug-O-War" Gauntlets. Both of her opponents stated that Beth had the advantage over them because she weighed more than they did.
- Jillian tells Kina that Susie and Cara approached her for an alliance with the other team, starting a rivalry between Cara and Kina.
- After losing a challenge, Beth quit the Beach Brawl wrestling challenge against Aneesa, claiming it was "against her moral values", thus leading to a segue in which host T.J. Lavin stated, "I thought I told you to quit two weeks ago when the other quitters quit". The other cast members speculated that she was afraid of losing to Aneesa, who was praying for the Beach Brawl challenge.
- Controversy arose amongst the Rookies team when Kina chose to go against Jillian in the final Gauntlet as opposed to Ibis, whom some of the Rookies believed to be a weaker player.
- On the reunion show, Mark announced his retirement from the Challenges. He gave his bandana to Derrick saying, "From the first Road Ruler to the last Road Ruler, I give you my bandana." Mark joins Mike "The Miz" Mizanin and Eric Nies and Timmy Beggy as the only cast members to officially issue a "retirement" from the Challenges. However, Mark would come out of retirement for The Duel 2 in 2009 and Battle of the Exes in 2012.
- Jamie was mistakenly cast as a Rookie when he had previously been on two challenges. (Extreme Challenge and Battle of the Sexes).
- On the final men's Gauntlet day, Timmy volunteered to face off against Derrick in the final men's Gauntlet, even though Derrick had stated he wanted David to go in. After two ties, with Katie and Aneesa opting not to vote, Timmy ultimately went in after time ran out and he told T.J. he wanted to go in. Despite stating beforehand that he did not even want to win, Timmy went on to win the Gauntlet, dethroning Derrick (who had already won 4 Gauntlet rounds), the Veterans' male captain, the day before the final challenge.
- The final Veterans were Aneesa, David, Julie, Katie, Mark, Robin, and Timmy.
- The final Rookies were Alton, Ibis, Jamie, Jodi, Kina, Landon, MJ, Randy, and Susie.
- The final captains were Alton, Aneesa, Kina, and Timmy.
- David, Julie, Katie, Mark, Robin, Ibis, Jamie, Jo, Jodi, Landon, MJ, Randy, and Susie never stepped into the Gauntlet.