MMA most satisfying defeats...

Shinya Aoki fought a kickboxer in a modified rules match. The first round was kickboxing and the second round was MMA. Shinya Aoki just flopped to his back and went for takedowns during the entire kickboxing round. I guess his reasoning was he didn't care if he got punished and lost points because he was sure he'd get the submission during the MMA round. So, he was just breaking rules constantly to survive the round.

I've never been more angry while watching a fight. It was like Werdum vs Overeem in Strikeforce but 10 times worse.

The kickboxer went for a flying knee during the MMA round and knocked him out cold in 4 seconds. Seeing that felt better than sex.

Wikipedia said:
Aoki faced K-1 kickboxer Yuichiro "Jienotsu" Nagashima in a special rules exhibition bout at Dynamite!! 2010.[26] In the first 3-minute kickboxing round, Aoki evaded Nagashima's offense by breaking the rules via excessive clinching, falling to the ground, and going for takedowns in order to run out the clock and move onto the 5-minute mixed martial arts round. Aoki was warned repeatedly by the referee, however no points were deducted as there could not be a decision winner. The commentary team of Michael Schiavello and Frank Trigg were openly criticising Aoki for his rule breaking during the first round, while the Japanese crowd uncharacteristically booed him. At 0:04 of the second MMA rules round, Aoki was knocked out immediately as he went for a double leg takedown via flying knee and subsequent grounded strikes.
 
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