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Lewis, meanwhile, stepped into the squared circle with Holyfield in March 1999 before having the rematch in November of that year.
The 55-year-old picked up a draw in their first encounter at Madison Square Garden, but Lewis would ultimately win by unanimous decision in the second fight.
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Posting on Instagram, Lewis extensively outlined the reasons for why he held Holyfield in high regards and why he named him as his toughest opponent of all time.
"People seem to be genuinely surprised when I tell them [Holyfield] was my toughest opponent, not to be confused with my toughest fight, which was [Ray] Mercer, but when you really dive into why that is, it actually makes a lot of sense," he said.