His next fight came against another highly regarded jiu jitsu fighter Paulo Filho, however in this fight despite some aggression and relative success in striking on the feet, Filho proved to be the far better grappler, as he got a submission victory.
He fought former WEC Middleweight Champion Paulo Filho on July 20, 2009 at Dream 10.
A rematch for the WEC Middlweight Championship between champion Paulo Filho and Chael Sonnen was advertised for this event, but Filho dropped out three weeks prior to the fight for personal reasons.
Kondo then received his second consecutive unanimous decision loss in his debut for the DEEP organization in Japan against Paulo Filho.
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