10. Evander Holyfield VS George Foreman – (1991) $35,300,000 pro-rated ($20,000,000) in “The Battle of the Ages”
The nineties saw the heavyweights take center stage again, because of one man, Mike Tyson. Holyfield, no slouch himself, benefitted greatly from the new found riches in the heavyweight division and perhaps used this fight as a tune-up to his upcoming rumbles with Tyson himself. Foreman, who along with Ali fought one of the biggest battles ever a few decades earlier, was still a 42-year-old beast who held a perfect 24-0 mark since coming out of his decade long retirement a few years earlier. One would think that the fight was a mismatch, but George held his own, and reminiscent of the first great Rocky Film, Foreman managed to withstand a flurry of punches in the seventh round only to keep holding his ground, until he managed to last the distance against all odds. And just like Rocky, he would become the champion a few years later. The oldest heavyweight champion in history.