For the first defense of his Ultimate Fighting Championship middleweight title, at UFC 199 Luke Rockhold was scheduled to grant a rematch to the man he had defeated to win the belt, Chris Weidman. Considering that Weidman had been a three-time defending champ and that their fight had been competitive until the fourth-round knockout, it seemed a perfectly sensible booking.
However, on May 17, 2016, less than three weeks before the event, the chronically injured Weidman withdrew with a herniated disc in his neck. The UFC’s first stated choice to replace Weidman was Ronaldo Souza. As short-notice replacements go, “Jacare” was both deserving and more intriguing than most, as he and Rockhold had history; five years earlier, Rockhold had defeated Souza to win the Strikeforce middleweight title. That fight had been competitive, and Souza had gone 9-1 since then, with the only loss a contentious split decision to fellow Top 5 middleweight Yoel Romero.
Unfortunately, Souza had fought just days earlier, and in the four and a half minutes it took him to pound out Vitor Belfort, had managed to tear cartilage in his knee. And thus it was that Michael Bisping received the call, on May 18, to face Rockhold on June 4 in the main event of UFC 199, in his adoptive hometown of Los Angeles. The matchup did not fire fans' expectations, to put it mildly. While Bisping was on a modest three-fight winning streak, it was over C.B. Dollaway, Thales Leites and the 2016 edition of Anderson Silva—who nearly knocked Bisping out. Worse yet, his last loss before that win streak had been a humiliating thrashing by none other than Rockhold, who had stunned Bisping with a head kick before finishing him with a one-armed guillotine from mount. That first meeting had been barely 18 months ago, and the mental image of Rockhold choking Bisping out while essentially striking a victory pose was too fresh in the memory to install the veteran Brit as anything other than a prohibitive underdog.
Of course, Bisping shocked the world that night, knocking Rockhold out with a huge left hook and a flurry of follow-up punches at 3:36 of the first round. By doing so in his 25th UFC fight, “The Count” set a record for the longest career with the promotion before winning a title, and at age 36, he was also among the oldest first-time champs in UFC history.
Bisping’s defeat of Rockhold at UFC 199 is not the greatest upset in UFC history from an odds standpoint, nor is it even the greatest title upset; Matt Serra-Georges St. Pierre I, Frankie Edgar-B.J. Penn I and Holly Holm-Ronda Rousey all featured greater betting underdogs pulling off the improbable. However, from a subjective standpoint, it’s possible to argue that Bisping’s self-described “Left Hook Larry” moment felt like a bigger upset. There was the lopsided and relatively recent first meeting between the two, as well as the short notice for the challenger while the champ had had a full camp. Most of all, there was the fact that going into the fight, Bisping appeared to have no plausible avenues to victory; in order to win, he showed one-punch power of a kind he had not really exhibited at any point in 35 career fights.
Bisping’s middleweight title reign was relatively short; his first defense was against Dan Henderson, who had memorably knocked him out at UFC 100, but otherwise had little to recommend him for a title shot at age 46. After winning a decision against “Hendo” (and sending him into retirement), Bisping became a part of history again, as former welterweight king St. Pierre came out of a four-year retirement to choke him unconscious at UFC 217, becoming just the fourth two-division champ in UFC history.