Mike Tyson argues with his coach following his fight with Orlin Norris, inset retro banner Credit: JOHN GURZINSKI/AFP via Getty Images

Mike Tyson was separated by countless security from opponent who later tried to sue him for $2 million

Originally posted on Bloody Elbow | By Kyle Dimond | Last updated Oct 23, 2025 1:42 PM ET

Mike Tyson’s series of controversial fights continued on this day in 1999.

While Tyson’s iconic knockouts in the heavyweight division will always see him remembered as a boxing icon, he also had numerous disappointing bouts.

‘Iron Mike’ always had a reputation for ending the night early, which is why you couldn’t afford to miss any of his fights or look away from the screen.

Tyson continued to put opponents away in style after two of his most significant defeats in 1996 and 1997, but for several years, all of his outings were overshadowed by a different talking point.

Photo by Jeffrey Asher/ Getty Images

Mike Tyson was left frustrated after his fight with Orlin Norris ended in a no contest

While both Mike Tyson and Evander Holyfield were criticized for using dirty tactics in their two fights, ‘Iron Mike’ certainly came off worse in their 1997 rematch.

A year and a half on from him biting Holyfield and being disqualified in the third round, the former champion faced off with Francois Botha.

Tyson secured the win but an assault charge and four-month prison sentence shortly followed this and prevented him from building any momentum.

Photo by Michael Tullberg/Getty Images

The feared knockout artist returned to the ring on October 23, 1999, where he faced off with Orlin Norris at the MGM Grand Garden Arena in Paradise, Nevada.

While Tyson did drop Norris with a huge shot in the first round, it was clearly thrown after the bell, which led to the mainstream star being deducted two points.

However, after Norris didn’t make his way to the center of the ring for the start of the second round, the fight was ruled a no contest due to him claiming to have injured his knee when he was dropped by Tyson.

In order to stop Tyson from creating any more controversy, countless members of security immediately flooded the ring to stop him from getting to his opponent once he became visibly frustrated.

Photo credit should read JOHN GURZINSKI/AFP via Getty Images

Orlin Norris attempted to sue Mike Tyson after their planned rematch didn’t happen

Both Mike Tyson and Orlin Norris appeared to be preparing for a rematch, with December mentioned as a possible timeframe during the post-fight interviews inside the ring.

However, Tyson later changed direction, going on to face Julius Francis at the MEN Arena in Manchester, England in January of 2000 instead.

As a result, Norris attempted to sue his former foe for $2 million for allegedly breaking an agreement they’d made for the rematch where he would’ve earned this amount as his purse.

Norris’ request was turned down by a judge, while ‘Iron Mike’ received his full purse from their first encounter after it was initially withheld by the Nevada State Athletic Commission.

This article first appeared on Bloody Elbow and was syndicated with permission.

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