Third UFC run
Shortly after the UFC 133 pre-fight press conference, Dana White commented on the potential to bring Henderson back to the UFC for a third go-around. "We'll see what happens," White said on Thursday in Philadelphia. "'Hendo and I have had some history in dealing. We'll see if we can figure something out and get him back in the UFC." Later Henderson commented, "I think the biggest fight they could promote is probably a title unification with whoever is the champ in the UFC."
Henderson faced Maurício Rua on November 19, 2011, at UFC 139 for his third run in the UFC. He won the bout via unanimous decision. The back and forth action earned both fighters Fight of the Night honors, and was described by many as one of the greatest fights in UFC history.
UFC President Dana White announced during the post-fight press conference of UFC 145 that Henderson would be the next opponent for Light Heavyweight Champion Jon Jones.
The bout with Jones was expected to take place on September 1, 2012, at UFC 151. However, Henderson withdrew from the fight citing a knee injury, and the remainder of the fight card was cancelled.
Henderson faced Lyoto Machida on February 23, 2013, at UFC 157. He lost the bout via split decision.
Henderson faced Rashad Evans on June 15, 2013, in the main event at UFC 161. He lost via split decision.
Henderson faced Vitor Belfort in a rematch on November 9, 2013, at UFC Fight Night 32. Henderson defeated Belfort in their first encounter in 2006 at Pride 32 via unanimous decision. He lost the fight via knockout in the first round, marking the first time in his MMA career that he had been stopped due to strikes. The match with Belfort was the last fight of Henderson's contract with UFC. On January 22, Henderson revealed to UFC Tonight that he signed a new, six-fight contract with the UFC.
In January 2014, a rematch with Maurício Rua was announced to take place on March 23, 2014, at UFC Fight Night 38. Despite losing the first two rounds after being knocked down by Rua, Henderson rallied back in the third round and won the fight via TKO due to punches. The win also earned Henderson his third Fight of the Night bonus and first Performance of the Night bonus.
Making a quick return to the cage, Henderson faced a much larger Daniel Cormier on May 24, 2014, at UFC 173. He lost the fight via submission (technical submission/rear-naked choke) in the third round after being out-wrestled and held down on the bottom for the majority of the fight.
On November 12, 2014, the UFC announced that Henderson would move down to Middleweight to face Gegard Mousasi on January 24, 2015, in the co-main event at UFC on Fox 14. He lost the fight via TKO in the first round.
Henderson faced Tim Boetsch on June 6, 2015, in the main event at UFC Fight Night 68. He won the fight via knockout at 28 seconds of the first round.
Henderson faced Vitor Belfort in a rubber match in the main event at UFC Fight Night 77. He again lost the bout via a combination of head kick and punches.
A rematch with Lyoto Machida was expected to take place at Middleweight on April 16, 2016, at UFC on Fox 19. However, on April 13, the UFC announced that Machida declared the usage of a banned substance during an out-of-competition sample collection last week. Machida stated that he was unaware that the substance was prohibited both in and out of competition. Therefore, he was removed from the bout and Henderson was re-booked for another event at a later date.
Henderson was quickly rescheduled to face Héctor Lombard on June 4, 2016, at UFC 199. He won the fight via knockout in the second round via a head kick followed by a reverse elbow and earned himself a Performance of the Night bonus, as well as becoming the first fighter to knock Lombard out cold.
Henderson faced then UFC Middleweight Champion Michael Bisping, in a rematch on October 8, 2016, at UFC 204. Despite dropping and nearly finishing Bisping in both the first and second round, he wound up losing the back and forth fight via unanimous decision. Both fighters were awarded Fight of the Night for their performance. At the conclusion of the fight, Henderson confirmed his intention to retire from fighting.
Dan Henderson was inducted into the Fight Wing of the UFC Hall of Fame at the UFC Fan Expo on July 5, 2018, alongside Maurício Rua, for their fight in 2011.