With 1.6 million pay-per-view buys, UFC 100 was the biggest event in the promotion's history until UFC 202 in August, featuring Conor McGregor's rematch against Nate Diaz, broke the record with 1.65 million buys. It was also Bisping's first title eliminator. The stage could not have been bigger.
"And I get knocked out in the most vicious way possible," Bisping said in the documentary "Michael Bisping: My Destiny," set to air this week ahead of Saturday's rematch with Henderson headlining UFC 204 in Manchester, England.
Heading into their first fight on July 11, 2009, Bisping's career was red-hot. He won the third season of "The Ultimate Fighter" reality series and a six-figure UFC contract in 2006 and was making waves and going through the rankings. He was also earning the kind of money to finally give his wife and children the life they had dreamed of since he quit his job as a factory worker in the English market town of Clitheroe, Lancashire, and began tearing through the U.K. MMA scene undefeated.
After moving down to middleweight in the UFC, Bisping immediately set his eyes on becoming champion. He went 3-0 and was told he would be given a title shot if he won against Henderson, who was then one month shy of his 39th birthday. With bad blood having brewed between them since their time as opposing coaches in season nine of "TUF," there was plenty of trash talk from Bisping in the buildup.
But Henderson had the last laugh at the Mandalay Bay Events Center in Las Vegas. Springing forward, he caught Bisping cold with his trademark right hand -- a punch that has been nicknamed the "H Bomb" -- to end the fight, adding one more punch for good measure while Bisping was on his back, before the referee jumped in to stop it. The sight of Bisping falling limp to the canvas has become one of the most iconic images in the UFC's 23-year history.
"I knew what people were saying about me -- he's done, he's finished," Bisping said. "That pissed me right off. I knew I wasn't done."
With the attitude that he still had a lot of fight left in him, Bisping was inspired to keep going.
"It's one of the things that I respect about Bisping, to get beaten that dominantly, then pick yourself back up and start fighting your way to the top again," UFC president Dana White said. "That's Bisping's mentality."
Bisping would fight nearly seven more years of ups and downs, including another two agonizing title eliminator defeats. First, he suffered a career-threatening injury when a tremendous high kick from Vitor Belfort detached his retina at a UFC event in Brazil in January 2013.
"I was unlucky with that," he said. "Everything that can go wrong with an eye went wrong. It was one thing after the other. It was over a year, [I] sat there doing nothing. You miss that excitement, you miss that thrill. You miss being in the thick of it all. I wasn't sure if I was ever gonna fight again. Fortunately, the doctors did a great job. I had a number of surgeries, passed medicals. I could still fight."
Then came a second-round submission defeat to Luke Rockhold at UFC Fight Night in Australia in November 2014. His self-confidence finally wavered. When UFC commentator Dan Hardy stepped into the Octagon to interview Bisping, he noticed something new.
"That was the first time I saw a question in his eyes," Hardy said. "That was the first time he looked like, 'Maybe I'm not gonna make it.'"
"After the Rockhold loss, there were times there that I never thought I was gonna get a title shot," he said.
But, after Chris Weidman pulled out of a rematch against new champion Rockhold at UFC 199 in June, Bisping took the fight on two weeks' notice. At age 37, in his 26th bout in the Octagon and his first in a title bout, Bisping rocked Rockhold in a stunning first-round upset.
"I knew it was my destiny," said Bisping, a child prodigy in jiu-jitsu from age 8. "That's powerful words. But if you have that vision in your mind, and you go out there and put the hard work in, make the sacrifices -- and with a bit of luck -- your destiny might just come true."
White didn't even have his jacket on, but "freaked out" and ran into the Octagon to congratulate Bisping on his fairytale win.
"I've known Bisping for so long, I know how hard he has worked to get there and to win that title," White said. "So I wanted to be out there, and I wanted to put the belt on him. To see him finally achieve the one thing he really wanted to achieve, it was a special night. I was happy for him."
For Bisping's first defense, the UFC's choice of opponent could not have been for poetic. He faces the now 46-year-old Henderson at the Manchester Arena on Saturday, with a chance to avenge that first setback of his career in front of a home crowd.
Bisping claimed during a media event Tuesday that he couldn't bring himself to watch the 2009 knockout loss to Henderson until the rematch was booked. He was finally forced to sit on his sofa at his California home and analyze what went wrong.
"My wife [Rebecca] sat next to me -- she was watching it, and I said, 'Oh my god. Jesus. Turn this off. Turn this off,'" Bisping said. "We all have bad nights at the office. That was a good night at the office for Dan; it was a terrible night for me. What can you say?
"Of course, I wanted to see what happened. It was seven years ago. But it didn't resemble me at all. I'd had many fights going into that fight, and that's not how I fight."
Bisping insists he is a different fighter from the one who was brutally dispatched in 2009, and that Henderson, a former user of the now-banned testosterone replacement therapy, will not be the same either.
"I'm much improved mentally and physically; Dan Henderson is kind of the opposite," he said. "He's not on the steroids, he's older. If you look at the muscle mass he had in that fight compared to now, it's like two different fighters.
"This isn't even a rematch, because the two versions of ourselves are so completely different. This is Michael Bisping 2016 versus Dan Henderson 2016, because it's two completely different fights."