Kimbo has been training with Bas Rutten for a while now so he's not the same fighter we've seen on Youtube or even in his first couple MMA bouts. I think Shamrock will get ktfo in the second round... maybe even the first.
However, with Bas Rutten in his corner, I wouldn't be suprised if Kimbo wins by submission. I think this would be a great strategy for Kimbo because Shamrock is a submisison expert. Thus submitting Shamrock would completely legitimize Kimbo as a world-class MMA fighter.
I respect Shamrock's skill, and he's one of the guys that I give credit to for shooting MMA into the stratosphere... however, I think he's lost his edge. Unfortunately, his age caught up with him. What happened to his flexibility, speed and athleticism? I remember from one of his fights with Ortiz, when Shamrock tried for an axe kick and his feet went out from underneath him. I enjoy watching him fight in classic UFC... but it's time for him to retire. Besides... I think he's a bit of a dick anyway... way too cocky and a bit of a mouth. However, his book "Into the Lions Den" was a great read.
I think the better fight would be Kimbo vs. Frank Shamrock.
I predict a similar outcome with Couture vs. Lesnar. Couture is 45 years old for crying out loud.
Granted... he could kick my ass with both hands tied behind his back, he's one of the greatest MMA fighters ever, and he's still got his tools... but shit man... Brock Lesnar is a freakin monster! Sure, Lesnar is a bit green, but he has the work ethic and financial wear-with-all, to catch up with the top fighters, real f'ing quick.
Couture is f'ing great... but I expect Lesnar to ground and pound him to a TKO within the first round.
I see Brock Lesnar doing to MMA, what Mike Tyson did to Boxing in the early 80s.
Anyway... that's my 2 cents...