8. James Toney
James Toney already had a stellar career in boxing before his lone MMA fight at UFC 118.
When the UFC announced they had signed the then-past his prime former boxing champ, it was a bit of a head-scratcher. He had zero ground game to fall back on and had seemingly gotten a bit out of shape since his championship days.
While many strikers like “Rampage” Jackson offered their services in welcoming Toney to the cage, the former boxer would end up drawing a much more difficult opponent for his Octagon debut.
Toney took on former UFC light heavyweight and heavyweight champion Randy Couture in Boston, and the result was about as predictable as could be.
Couture wasted no time in taking down the boxer, completing the takedown with an ankle pick against a bewildered Toney. “The Natural” softened him up for a minute or two before mercifully submitting Toney with an arm-triangle choke just minutes into round one.
Toney would eventually return to boxing and never fought in MMA again. But with all this Mayweather vs McGregor talk lately, it’s interesting to see how far back this intersport rivalry goes.