10 Legendary MMA Bouts Where Both Fighter's Careers Never Recovered

Ken Shamrock fought well past his prime and, as such, suffered some tough setbacks later in his career. That being said, in his heyday, Shamrock came very close to living up to his 'World's Most Dangerous Man' moniker.

The UFC 1 vet has beaten legends like Bas Rutten, Maurice, Smith, and Dan Severn on his road to being inducted into the UFC Hall of Fame. Still, his overall record of 28-17-2 is somewhat uninspiring.

Shamrock's 2002 Pride 19 bout with fellow UFC Hall of Famer Don 'The Predator' Frye appeared to be a turning point in both men's careers. In fact, Frye was quoted as saying, “All I know is that Ken Shamrock and I both left something in the ring that night. And neither one of us have been the same since. I don't know if he will admit it, but I’ll admit it.”

During the highly competitive matchup, Shamrock cinched in multiple submissions including a kneebar and a pair of ankle locks, but Fyre simply refused to tap. 'The Predator' would end landing several solid shots and even knocked Shamrock to the mat, which helped him earn a split-decision win. Though Frye emerged the victor, his ankle was badly injured, which caused him to become dependent on painkillers.

Frye would fight on but was no longer the same menacing athlete that stepped into the ring at Pride 19. Heading into the fight he was sporting an impressive 14-1 record. Following Pride 19, the UFC 8 tournament winner would go 6-8-1, before retiring in 2011.

Shamrock would continue to compete until 2016 and went 3-10 during the remainder of his career.