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I don't think either of those Heavyweight fights should be considered for the simple fact that anyone can knock out anyone in that weight class.I wont include Fedor vs Maldonado because tech. It isnt a loss.
Silva L to Takase
Fedor L to Bigfoot
GSP L to Serra
Stipe L to struve
Imo, has to Be Silva vs Takase. Takase is like 6 and 7.
Which means it comes down to Silva and GSP's respective losses:
Silva was 11-1 and Takase was 4-7-1 at the time of their fight; Silva was essentially dominated on the ground and then submitted.
GSP was 13-1 and Serra was 9-4 at the time of their fight; GSP was winning the stand-up until he got caught with a right hand.
Silva's loss to Takase is probably the worst of the four options presented.