It is a weird year for UFC—fantasy bookings, bitter rematches, hot potato championship victories, a surprise return, one strange debut and an impending retirement. Dan Henderson and Michael Bisping will fight tooth and nail in the main-event of UFC 204 for the Middleweight Championship. It is one of those fights based less on merit and more on the former glory of the challenger.

UFC 204 Preview

Henderson, 46, is a tough veteran of the game, but his glory has vaned just more significantly in the past five years. He has failed to win two consecutive fights since then. And it is more out of a gratitude by the authorities and to appease the fans that he is getting a championship match at his age. He has been vocal about his retirement this year and has iterated his interest in retiring with the gold.

Though he has also stated that a win or a loss won’t make a difference, that he will hang up his gloves after October 8 in Bisping’s home turf of England. Even though the decision to allow him to jump the line has been critiqued a lot, his brutal win over Hector Lombard at UFC 199 was really convincing. In a normal case a record of 3-6 of past four years would normally not get any fighter close to a title shot, but the bad blood from Henderson’s first encounter with Bisping from UFC 100 has made the fans really eager for a rematch.

Henderson won that bout by KO, dropping Bisping with huge right hands and delivering strikes while he fixed his back on the mat. This KO and follow up still remains afresh in the memories of audiences as one of the defining moment of the sport.

Former Champion Chris Weidman was scheduled for a fight against Luke Rockhold at UFC 199 but was pulled out of the event just two weeks before the fight. Bisping served as the subbing and stunned Rockhold cold to capture the belt in a memorable first-round knockout. It was then that the rumors began to emerge of pairing Henderson and Bisping, as both emerged as winners the same night.

A retrospective look in to Dan Henderson’s defining moments

Henderson has carved out a legendary career, fighting the best in the business amid wins and losses. And his next fight will be no different. With a crushing right hand, granite chin and Olympic-level wrestling, former Pride and Strikeforce Champion Dan Henderson has found tremendous success throughout his 20-year old mixed martial arts (MMA) career.

Hendo became the first fighter in the history of the sport to win two titles simultaneously in separate divisions, holding the PRIDE Welterweight and Middleweight Championships. He is a legend and there isn’t much he hasn’t done with the exception of hoisting an Ultimate Fighting Championship belt up in the air.

He competed for the middleweight and light heavyweight championships upon his return to the Octagon in 2007, losing back-to-back contests to Quinton Jackson and Anderson Silva, respectively. These two defeats were the hiccups he had had along the way. Like every veteran, he dropped matches he was meant to win and turned far away from golden boy with perfection matches. He was once labelled ‘Decision Dan” whose fights were less flattering for the fans who crave for spectacular finishes. We travel back to present to you the fights which have defined his career, as he prepares to fight one last time and possibly accomplish what he hasn’t in two decades.

Dan Henderson vs. Murilo Bustamante
PRIDE Shockwave 2005
Dec. 31, 2005

Pride FC had big plans for Murilo Bustamante when it lured the Brazilian jiu-jitsu ace away from UFC shortly after he successfully defended his middleweight belt for the first and only time against Matt Lindland in 2003. However, he got off to a rocky start, losing three consecutive fights, including a technical knockout finish at the heavy hands of Henderson. In 2005, he entered the Pride FC Welterweight Grand Prix, stringing together two straight victories and securing a spot in the final opposite Henderson, who literally punched his ticket to the championship fight with two knockout wins in the opening and semifinal rounds. But once again, it was Henderson who would prevail, earning a split decision from the judges and taking home the 185-pound tournament trophy, as well as the division championship. Another Henderson hardware haul.

Dan Henderson vs. Wanderlei Silva
PRIDE 33: “Second Coming”
Feb. 24, 2007

For most of his career, Henderson was a two-division fighter, stuck between the 185 and 205 pound weight classes. However, he was much more successful against lighter competition. Losses to Ricardo Arona, Antonio Rodrigo Nogueira and his brother, Antonio Rogerio Nogueira, made it seem pretty clear that Henderson was in over his head in the 205-pound division. He’d start to change that perception, however, when he decisioned Vitor Belfort at Pride 32: “The Real Deal” in 2006. And he’d prove it wrong altogether when he scored an improbable, and devastating, knockout of Wanderlei Silva in their rematch four months later.

Earlier in their careers, “The Axe Murderer” registered a unanimous decision win over Henderson. He would go on an epic championship run, successfully defending his middleweight title several times over the next six years. That would come to a crashing end when Henderson separated him from consciousness with a blistering left hand on the button, which came shortly after a highlight-reel spinning backfist that wobbled the Brazilian. It marked the first time ever in MMA competition that a fighter held two major titles at the same time in different divisions. Dan Henderson, setting records at 36.

Dan Henderson vs. Michael Bisping
UFC 100: “Lesnar vs. Mir 2”
July 11, 2009

It was the centennial event for UFC. It was a hallmark in the history of the promotion, which was headlined by its two biggest draws, heavyweight champion Brock Lesnar and 170-pound deity Georges St. Pierre. Henderson was also on the card, taking on the polarizing Michael Bisping, the culmination of their “U.S. vs. U.K.” coaching rivalry on the set of The Ultimate Fighter (TUF) 9.

“The Count” was a viable and marketable middleweight contender at the time, and if he could defeat Henderson, was likely guaranteed a title shot against division champion Anderson Silva in the near future. Henderson detonated those hopes with a thundering right hook, which he followed up with a flying face forearm smash as Bisping lay supine, stiff as a board, on the canvas. It was the biggest highlight on the UFC’s biggest ever show. Henderson stole the show, scoring one of the greatest, career-defining knockouts ever against one of the sport’s most reviled personalities.

Dan Henderson vs. Rafael Cavalcante
Strikeforce: “Feijao vs. Henderson”
March 5, 2011

After his epic win over Bisping, with his stock at an all-time high, Henderson opted to walk away from the UFC after the parties failed to agree on the terms of a contract extension. Strikeforce quickly swooped in and signed him to a deal, as well as rewarded him with an instant title shot against middleweight champion Jake Shields. Despite a marked experience and size advantage, Henderson would drop a disappointing five-round unanimous decision, even though he nearly finished the fight in the first round.

He would rebound with a rematch against Sobral in a light heavyweight number one contender eliminator match in his next fight, more than a decade after their first encounter. He would quickly get back in the knockout win column and earn a crack atRafael Cavalcante’s 205-pound belt. It took him three rounds, but Henderson eventually connected with a flurry of powerful punches that led to a technical knockout stoppage. He was once again crowned champion at the ripe age of 40. An accomplishment that seemingly never gets tired, especially when it happens at such an advanced stage of a career. Old man strength prevails once again.

He conquered at 40, and his hunger for success still keeps him driving further and challenge his limits. It is now known that it will be his last fight ever at the UFC 204, will he manage to finish on a high note and make it 2-0 against Bisping or will Bisping succeed in avenging his KO defeat from UFC 100.

Don’t forget to watch the epic conclusion of this battle at UFC 204 on October 8, 2016 live from Manchester, England. Stay tuned for the updates from aftermath.