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He fought former WEC Middleweight Champion Paulo Filho on July 20, 2009 at Dream 10.
Massenzio then missed several months, before facing former WEC Light Heavyweight Champion Brian Stann, who was making his middleweight debut, on August 1, 2010 at UFC on Versus 2.
He rematched Brian Stann, the man he defeated to become the last reigning WEC Light Heavyweight Champion for the second time at UFC Fight Night 19, Cantwell lost the rubber match via unanimous decision.