Tim Sylvia
On November 18, 2006, at UFC 65, Monson fought Tim Sylvia for the UFC Heavyweight Championship. He lost a five-round decision and would later ask to be released from his UFC contract in the hopes of facing then-PRIDE Heavyweight Champion Fedor Emelianenko at a BodogFIGHT scheduled for March 2007. However, negotiations fell through and the match did not happen during that time.