Still praying the Wanderlei Silva vs. Chuck Liddell fight happens! (It probably won't though
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All the talk about Wanderlei beat Rampage ,Rampage beat Chuck and Chuck beat Tito and Tito beat Wanderlei stuff means very little. First off a lot of those fights happened a long time ago and the fighters have evolved since then. Second, styles make fights. Beating a common opponent means very little.
As for the fight itself, I think it could go either way. I think Wanderlei is overall the better fighter, however I think Chuck would win. Wanderlei is a devastating striker, but he tends to throw wide punches. Chuck could catch him with quicker straight punches much like CroCop did. A lot of the fight would depend on what would happen in the clinch. If Wanderlei could get a Thai clinch going, Chuck would be in for a world of pain. However Chuck is a much better wrestler than people give him credit for. He could hold his own in the clinch and if the fight goes to the ground.