Mike Tyson had an incredible winning streak at the start of his boxing career, dominating like nobody had seen before in the sport.
The legendary fighter won his first 37 fights in a row, decimating opponents with a series of quick knockouts that made his fights must-see pay-per-views.
This run saw Mike Tyson called one of the greatest heavyweight boxers of all time, alongside legends like Muhammad Ali and Joe Louis.
However, before he became a phenom in the ring, a man Tyson dismantled in minutes beat him twice during his amateur career.
Henry Tillman beat Mike Tyson twice as an amateur before being knocked out in the first round
It’s rare that anybody can claim to have beaten Tyson in a boxing match, and even rarer to boast to have done it twice.
Henry Tillman is part of a rare breed of fighters who have those wins on their résumé, with only Evander Holyfield matching him during his professional career.
Tyson knocked Tillman out in the first round of their 1990 clash, just months after Tyson’s shock loss to Buster Douglas in one of the biggest upsets in boxing history.
That win proved to be sweet revenge for Tyson, who lost to Tillman twice as an amateur before he became the legend he would be in the professional game.
The pair fought twice in the build-up to the 1984 Olympics, aiming to be part of Team USA competing at the event held in Los Angeles that year.
The first bout saw Tyson dropping Tillman, although the less-experienced Tillman won the fight by a split decision.
In the rematch, Tillman won the same way to earn his place on Team USA and crush Tyson’s dreams of fighting at the Olympic Games.
The bout didn’t include any knockdowns, but Tillman learned from their earlier contest to use his size and reach advantage to keep the future world champion away from him.
It was a disciplined three rounds from Tillman, who did his best not to get involved in a punching match with Tyson, something he would undoubtedly lose.
Using the jab and cleverly clinching when needed, the second round went much the same. However, knowing he was losing on points, Tyson came out much more aggressive and took the fight to Tillman, giving him a preview of their bout years later.
He may have lost the fight and missed out on the Olympics, but Tyson learned a lot that would have helped him become the dominant champion he was in the years following.
Henry Tillman thinks his wins over Mike Tyson could have gone differently if he had known more about him
In an interview with The Mayweather Channel, Tillman recalled his two fights with Tyson as an amateur and admitted that the fights were not easy despite his victory.
He also admitted that he was vastly more inexperienced than Tyson at the time, and if he’d have known that fact, then the fight could have gone a lot differently.
“He’s a man-child. Tyson was knocking out people at 16, 17, 18 years old.” Tillman said.
“I beat him, but he still gave me the blue one easy — dropped me in the first. Nothing easy about that.
“At that time, I was so new to boxing. The things I know now, I probably wouldn’t have done as well back then.
“I was worried about certain things. I had stuff on my mind. I didn’t know that a guy with a hundred fights shouldn’t have been in the ring with me — I only had 15, 16.”
While he couldn’t carry on his undefeated record against Tyson into his professional career, Tillman still knows he got the best of the legend as an amateur.