In 2002 Bob Sapp made his K-1 kickboxing debut with a loss to Tsuyoshi Nakasako. However, he came back with a win in 77 seconds over the ferocious Cyril Abidi. Sapp followed that up with back to back wins over Ernesto Hoost.

The next year he suffered a broken eye orbit in a fight with Cro Cop, but came back with a win over Kimo Leopoldo at the K-1 World Grand Prix 2003, on August 13, 2003 in Las Vegas, Nevada.

Sapp was at the height of his success.

There was talk of a fight between him and former undisputed heavyweight boxing champion ‘Iron’ Mike Tyson. When Tyson came into the ring, Sapp took it as a challenge, and reacted with fury.

“I think Bob Sapp is awesome,” said Tyson in the ring. “He has awesome physical power. As I’ve said before, if we fight with the Marquis of Queensbury rules, I’d love to fight him … tonight.”

The pair had words and Tyson goaded Sapp.

“Sign the contract,” he crowed. “Sign the contract.”

K-1 signed Tyson to a contract and the fight appeared to be on. Unfortunately, Tyson’s status as a convicted felon made him unable to get a visa to fight in Japan, where the fight would have been most profitable. Other locations for the proposed fight were made, but the fight ultimately never happened.

Tyson went on to have two more fights, both in boxing. He lost both by KO, and retired.

Sapp continues to fight to this day, but has a highly unusual approach. He takes a fight, but explicitly quits if the thinks he will get hurt, and this is a hurting game.

In the past 10 years, Sapp lost 10 in a row. The he won one when his opponent broke a toe kicking Sapp. Then he lost three more. Most recently he beat Akebone via technical decision, under shootboxing rules.

Complete confrontation video: