#2 B.J. Penn
B.J. Penn should have called it a career when he lost his trilogy fight with Frankie Edgar in 2014. However, 'The Prodigy' continued his UFC run for five more years, ruining his professional record that now stands at 16-14-2.
Penn is considered one of the greatest lightweights of all time. He was the first UFC lightweight to defend his strap on three consecutive occasions. Thanks to his exploits inside the octagon, Dana White credits Penn behind the resurgence of the lightweight division that once looked incredibly mundane.
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Unfortunately, though, Penn couldn't perform at his best in the later stages of his career. After securing his second win over Matt Hughes in 2010, the Hawaiian competed in eight UFC fights. He lost seven of them, and drew one.
#1 Anderson Silva
Despite losing 11 MMA fights, Anderson Silva is still widely regarded one of the greatest fighters of all time. During his prime years, 'The Spider' was on a tear. He defended his belt on ten occasions after winning the strap in 2006.
Except Chael Sonnen, no one came close to dethroning the Brazilian until he bumped into Chris Weidman in 2014. While showboating, Silva found himself on the receiving end of a stinging punch from Weidman that sent him to the canvas.
In the rematch, Silva sustained a horrific leg break injury. It would have been a wise decision if 'The Spider' had considered hanging up his gloves immediately, but he decided to have another shot at the title he held for almost six years.
More than a year after his injury, Silva challenged Nick Diaz at UFC 183. Although he won the fight, the decision was later ruled a no-contest after the former champ tested positive for drostanolone and androsterone.
After that, Silva competed in six UFC fights. He was able to win only one of them, against Derek Brunson.