5. Ray Mercer knocks out Tim Sylvia
Well Tim, you really could have done better here.
Here is world champion boxer Ray Mercer fighting in his first ever professional mixed martial arts bout against 2x UFC heavyweight champion Tim Sylvia, what could happen here? Mercer did have one amateur fight before this however, when he was choked out by Kimbo Slice in just over a minute. Surely Tim Sylvia can do equally as well against a boxer untrained in mixed martial arts right? Nah, that’s not what happened. Mercer tagged Sylvia and knocked him out in 9 seconds.
Sylvia came out of this looking terrible but did manage to salvage some self-respect afterwards, winning 7 of his next 8 before falling apart again in 2013. Doctors finally declared Tim Sylvia unfit for competition in 2015.