Kimbo Slice had over 20 "internet street brawls" in his street fighting career. Only one ended in a loss.
In 2004 Kimbo faced off against a 33-year old Boston Police officer and former Golden Gloves champion named Sean Gannon. During the fight, the MMA trained Gannon, grappled and kicked Slice; which Kimbo's camp thought was against the rules that were laid out before hand. There was some controversy but eventually the fight went on and Kimbo was eventually knocked down for a thirty count.
The fight is a sore spot for Kimbo who wants nothing more to avenge his only loss.
"I would literally give my left nut—but I wouldn't tell anybody—to fight him again."
The fight would be a huge draw and will likely make for a hefty payday for Gannon, but he'll have to weigh out the possibility of possibly losing his job on the Boston Police Department if he participates, as the Boston PD has been less than agreeable to allowing Gannon to fight in MMA matches.
ESPN is reporting, however, that a fight agreement between EliteXC and Gannon is in the works and is likely to be signed by years end.