On November 13, 1992, at the Thomas and Mack Center in Las Vegas, Nevada, Evander ‘The Real Deal’ Holyfield fought Riddick ‘Big Daddy’ Bowe in the first of what would become a trilogy of not-to-be-forgotten bouts between the pair. Holyfield, 30, came into the fight as undisputed world heavyweight champion – having won the WBC, WBA and IBF titles with a third-round knockout of James ‘Buster’ Douglas at The Mirage, Las Vegas two years earlier – and unbeaten in all 28 professional matches. Bowe, 25, was similarly unbeaten, boasting 27 knockouts in his 31-fight professional career, but stood 3″ taller and weighed in 30lb heavier than Holyfield.

Unsurprisingly, granted his height, weight and reach advantage, Bowe landed the harder and more significant punches throughout the first nine rounds. Nevertheless, despite being outgunned, Holyfield refused to yield kept coming forward. Early in the tenth round – later hailed as ‘The Round of the Year’ by ‘The Ring’ – Bowe hurt his opponent with a right uppercut and, sensing blood, unleashed a flurry of punches which, at one point, Holyfield seemed unlikely to survive. Survive he did, though, and finished the round strongly.

In the eleventh round, Bowe hurt Holyfield again, with a left hook, and followed up with powerful right hand that knocked the champion off his feet. Holyfield survived that round, too, but by that stage the result had gone beyond recall; Bowe used his jab to good effect for the remainder of the contest and won, comfortably, by unanimous decision, 115-112, 117-110, 117-110.

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On November 9, 1996, ‘Iron’ Mike Tyson made the first defence of his World Boxing Association (WBA) Heavyweight Title against Evander ‘The Real Deal’ Holyfield at MGM Grand, Las Vegas. The bout was seen by many observers – including bookmakers, who initially quoted Holyfield at 25/1 – as little more than a formality for the self-styled ‘Baddest Man on the Planet’, against a washed up opponent.

Indeed, when Tyson landed a clean right hand, which sent Holyfield staggering across the ring, in the opening seconds, a quick, dramatic knockout looked on the cards. However, Holyfield refused to be intimidated, kept his head and landed some good shots of his own. Having connected several times in round one, he did so again in round two, with a straight left that stopped Tyson in his tracks.

Holyfield continued to crowd in on Tyson, removing the efficacy of his hook and, although caught with a ferocious right uppercut, which sent him backpeddling, in the fifth round, showed no sign of crumbling. In the sixth round, Tyson sustained a cut above his left eye from an accidental headbutt and as the chant of ‘Holyfield!’ rang out from the crowd, suffered just the second knockdown of his career.

Thereafter, Tyson appeared increasingly tired and lacking in confidence. Late in the tenth round, Holyfield connected with two powerful right hands, which sent Tyson stumbling across the ring. Dazed and unsteady on his feet, Tyson came out for the eleventh round, but lasted only 37 seconds, with the referee stepping in to stop the contest and hand Holyfield victory by technical knockout. The bout was named ‘Fight of the Year’ and ‘Upset of the Year’ by ‘The Ring’ magazine.

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