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Evander Holyfield has shared the ring with some of the greatest heavyweights of his generation.

But none of his opponents were more skilled, in his eyes, than Riddick Bowe.

Holyfield and Bowe shared an epic trilogy between 1992 and 1995
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Holyfield and Bowe shared an epic trilogy between 1992 and 1995Credit: AFP - Getty

“I would say Bowe. I had three fights with Bowe," Holyfield told Ring Magazine.

“He was very competitive. He was always going to be in shape when he fought me.”

Holyfield fought Bowe thrice between 1992 and 1995.

Their inaugural encounter in November 1992 at the Thomas & Mac Center in Las Vegas saw Bowe snatch the undisputed heavyweight titles from Holyfield via unanimous decision in a ferocious fight.

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'Big Daddy' put on a career-best showing as he dropped Holyfield in the 11th round en route to a 117–110, 117–110 and 115–112 points win.

In the immediate aftermath, Bowe was ordered by the WBC to defend his belts against Lennox Lewis, the man who had defeated him in the 1988 Olympic final.

However, Bowe chose to relinquish his WBC strap rather than face Lewis in an act of defiance that saw him throw the green and gold belt in the bin at a press conference.

After a couple of routine defences of his WBA and IBF titles against Michael Dokes and Jesse Ferguson, a rematch with Holyfield was made in November 1993.

This time, Holyfield returned the favour after another high-octane battle.

Farcical scenes unfolded in the seventh round when a paraglider crashed into the ring lights to the confused horror of everybody in attendance.

Lewis defeated Holyfield in a rematch after boxing to a draw previously
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Lewis defeated Holyfield in a rematch after boxing to a draw previouslyCredit: Getty

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The subsequent 17-minute delay gave Bowe, who was tiring by this point, the breather he desperately needed.

However, Holyfield was able to finish strong to get his hand raised via majority decision in what remains the only blemish on Bowe's otherwise perfect 43-1 record.

Two years later, Bowe and Holyfield met for a third time in a non-title fight after the 'Real Deal' was relieved of his world titles by Michael Moorer.

Holyfield dropped Bowe for the first time in his career in round six with a booming left hook, but 'Big Daddy' rallied to stop his adversary with a clubbing right in the eighth stanza.

Bowe's wins over Holyfield stand as the crowning achievements of a career that tapered off after their third fight.

Meanwhile, Holyfield learnt valuable lessons on how to fight bigger men from his trilogy with Bowe and built himself into the heavyweight he needed to be to go toe-to-toe with the giants of one of the glamour division's golden eras.

Mike Tyson boxing Evander Holyfield.
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Holyfield defeated Tyson twiceCredit: getty

In the years that followed his third clash with Bowe, Holyfield beat Mike Tyson twice and avenged his defeat to Moorer to become WBA and IBF champion before coming up short against WBC titlist Lewis for the undisputed crown.

He hung up his gloves in 2011 as a four-time world heavyweight champion after previously unifying the cruiserweight division in the late 1980s.

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