WWE owner Vince McMahon had put his faith in a batch of younger superstars, including beloved world champion Bret Hart and the flamboyant Shawn Michaels – two genuine backstage rivals who were tremendously loyal to the company. But heading into pay-per-view event Survivor Series at Montreal’s Molson Centre on Sunday 9 November there was a problem behind the scenes. A big problem.

Hart was to fight Michaels for the title in the main event in front of an arena full of Hart’s fellow Canadians. But, as his current contract neared expiry, the champion was unsure whether his future lay with WWE. With a policy of buying up their rivals’ top talent, WCW had made him a huge financial offer that was proving hard to turn down, even though he wanted to stay with the company he had served with distinction since 1984. Cue plenty of back-and-forth negotiations between Hart and Vince McMahon, as the pair desperately tried to broker a deal that would keep the superstar where he was.

A deal couldn’t be agreed. Hart gave his notice and the nightmare scenario for McMahon was coming true: one of his biggest draws leaving for WCW as WWE champion. But they reached a compromise of sorts. Hart would beat Michaels at Survivor Series via disqualification (real-life animosity between the pair meant neither was willing to lose outright to the other) and then relinquish the belt the following night on WWE programming in an emotional farewell. It was a solid plan that meant both parties would save face. Except Vince McMahon had other ideas…

As two athletic and technical grapplers who always laid everything on the line in the ring, Hart (above) and Michaels put on classic matches whenever they faced off. Survivor Series was no different, with each man giving their all in front of a pumped-up partisan crowd that loved Hart as much as they hated Michaels (as the heel, Texas native Michaels blew his nose in the Canadian flag upon entering the ring).

And then, with 12 minutes of the main event gone, one of the most talked-about moments in wrestling history unfolded. The disqualification finish still in place, Michaels angled Hart into Hart’s signature submission move, the sharpshooter. The idea was for the champion to counter the move, but before that could happen referee Earl Hebner signalled that Hart had submitted, losing the match and the title in the process. What was happening? This wasn’t how the match was supposed to end. This was a set-up.

The immediate fallout was chaotic. Hart, realising he had been ambushed, spat in the face of McMahon before spelling out WCW in the air with his finger, as jeers rang out around the arena. The fans were beyond furious. Meanwhile, an angry-looking Michaels was guided backstage, where things were about to get even more interesting.

After making his way behind the curtain, Vince McMahon locked himself in his temporary office with a handful of his cronies. Mark Calaway (aka The Undertaker) attempted to persuade WWE’s owner to come out and apologise immediately to Hart. Once McMahon emerged, a brief discussion with Hart in the locker room ended when the now former champion floored his boss with a punch. (Much of this is captured in the acclaimed behind-the-scenes documentary Hitman Hart: Wrestling With Shadows.)

If he had been brought down a peg or two in the minutes following the bout, Vince McMahon was in feistier spirits the following night. Sporting a black eye, he appeared on WWE programming and made the infamous claim that “Bret Hart screwed Bret Hart”, suggesting Hart’s decision to depart the company gave him no other choice but to get the belt by whatever means necessary. Hart eventually made the move to WCW, where his career never reached the heights it had in WWE. Meanwhile, Shawn Michaels (below) revealed years later he was in on the conspiracy all along, as did referee Earl Hebner, a close friend of Hart’s.

The effect the match had on the wrestling industry was monumental. It was the hottest story in the business. Making viewers question what they were seeing, it gave WWE some much-needed momentum in their ongoing battle with WCW. Putting all their creative focus on more authentic storylines thereafter, fans couldn’t get enough of the company’s gritty new approach – and with that came a boost in ratings. By the spring of 1999, WWE finally toppled WCW and never looked back.

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