Content on this page may include affiliate links. If you click and sign up/place a wager, we may receive compensation at no cost to you.
Mike Tyson is an underdog to Jake Paul: A betting history of Tyson’s boxing career
Tyson will be a betting underdog on Friday night for only the second time in his storied career
It is a testament to the sensational dominance Mike Tyson exhibited during his prime fighting years that when he steps into the ring on Friday night against Jake Paul, it will mark just the second time in a 56-fight pro career that he will do so as the betting underdog.
Aside from that one other occasion, it took him being eight years into AARP eligibility to do it. At 58 years old, Tyson is so far removed from his physical prime that he could practically be prime Tyson’s grandfather.
For more about the odds on Friday night’s fight and the best sportsbook deals for the bout, check out the best current sportsbook promotions.
Here’s a look at some notable boxing betting moments surrounding Tyson’s biggest fights.
Opponent: Trevor Berbick
Date: November 22, 1986
Location: Las Vegas, NV
Favorite: Tyson
Tyson’s odds: -300
For one of the first times in modern boxing history, a challenger, in this case Tyson, was a betting favorite to beat a reigning heavyweight champion. Tyson handled it with ease, blasting Berbick in just two rounds and becoming, at 20 years old, the youngest fighter ever to win a heavyweight championship. Tyson’s manager said later that Berbick was one of the guys they wanted to bump off on the way to the title.
Opponent: Larry Holmes
Date: January 22, 1988
Location: Atlantic City, NJ
Favorite: Tyson
Tyson’s odds: -800
Promoter Don King’s $3 million guarantee was enough to drag Holmes, the once-beaten former heavyweight champion, out of retirement. At 38, Holmes hadn’t fought since losing a disputed decision against Michael Spinks 22 months prior, but the temptation was too much. He tried to get some of his old mojo going, but Tyson bludgeoned him and knocked him out in the fourth round.
Opponent: Michael Spinks
Date: April 19, 1988
Location: Las Vegas, NV
Favorite: Tyson
Tyson’s odds: -400
Both Tyson and Spinks were undefeated, and both had claims to the heavyweight title. Spinks moved up to heavyweight and dethroned Larry Holmes after cleaning out a stacked light heavyweight division and despite the betting odds, many pundits picked him to outbox and decision Tyson. No chance. Spinks entered the ring looking terrified and was counted out 91 seconds later. Spinks never fought again.
Opponent: James “Buster” Douglas
Date: February 11, 1990
Location: Tokyo, Japan
Favorite: Tyson
Tyson’s odds: -4200
The American sporting public was getting so tired of Tyson’s quick knockouts that promoter Don King took the Tyson show on the road. Douglas seemed an especially poor choice for a title challenger. Despite a five-fight winning streak, losses to lesser heavyweights marked him as an easy night for Tyson. Instead, Douglas, inspired by the recent death of his mother, turned in the performance of a lifetime, outboxing Tyson and hurting him. Douglas survived a knockdown in the eighth round to win the heavyweight title by stopping Tyson in the 10th, resulting in one of the biggest upsets in sports history.
Opponent: Evander Holyfield
Date: June 28, 1997
Location: Las Vegas
Favorite: Tyson
Tyson’s odds: -200
In retrospect, the odds favoring Tyson were inexplicable. Holyfield, as a massive underdog, manhandled Tyson in their first fight and stopped him in the 11th round to claim a heavyweight championship. Still, the oddsmakers liked Tyson in the rematch, which was more competitive than the first fight but was going Holyfield’s way early when Tyson snapped, biting off a 1-inch piece of cartilage from the top of Holyfield’s ear and spitting it onto the canvas. Tyson promptly bit Holyfield again, prompting the referee Mills Lane to disqualify him.
Opponent: Lennox Lewis
Date: June 8, 2002
Location: Memphis, TN
Favorite: Lewis
Tyson’s odds: +200
Tyson rode four victories and two no-contests into his challenge of Lewis for a share of the heavyweight world championship. After a promising first round for Tyson, Lewis took over, pounding him from long range with right hands and jabs, which Tyson, then at 35 years old (Lewis was 36), was too slow to avoid and counter. He took a slow pounding before collapsing after a Lewis right cross in the eighth round and was counted out by referee Eddie Cotton.