#5 Kurt Angle vs. Brock Lesnar
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This one isn't really a one-sided matchup but anybody beating Brock Lesnar deserves to be on this list, and that's exactly why Kurt Angle makes it here. Despite Angle's pedigree as an Olympic gold medalist, Lesnar was adamant he could beat the veteran in a freestyle amateur wrestling contest due to his superior weight advantage.
Keeping in mind that Lesnar was himself a NCAA Champion, this was always going to be a tight affair. According to all sources who were present for this fight as well as Angle himself, the fight went on for nearly 15 minutes with Angle scoring the only takedown of the bout before Vince McMahon caught wind of what was happening and put a stop to it.
Lesnar, of course, never one to admit defeat – and especially not during a UFC interview – stated that he tapped Angle out in 10 seconds even though there are no submissions in freestyle wrestling. Nice try, Brock.
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