Gil Castillo fell short against one of the sport’s all-time greats. | Photo: Jeff Sherwood/Sherdog.com
7. Gil Castillo vs. Matt Hughes
UFC 40 “Vendetta” | Nov. 22, 2002 -- Las Vegas
Having nearly reached the pinnacle of the sport in just one bout at middleweight, Castillo elected to try his hand at 170 pounds. The Californian needed just one victory -- a unanimous verdict over Chris Brennan -- before he was targeted for a showdown with Hughes at the MGM Grand Garden Arena.
Fortunately, the bout was overshadowed by the grudge match between Ken Shamrock and Tito Ortiz, which received mainstream media attention in the days leading up to the event. Couple that big-ticket encounter with the presence of fan-favorite Chuck Liddell on the card and few people were concerned about Castillo’s questionable status as No. 1 contender.
In a lopsided bout, Hughes out-landed his foe by 35 total strikes in the opening round before the bout was called by the cageside physician due to a facial cut. Although it appeared the cut resulted from a head butt, Hughes was clearly in control and there was no sense of urgency to book a rematch. After two title shots in three UFC appearances, Castillo would not set foot in the Octagon again. His last bout, a first-round technical knockout defeat to Jake Ellenbeger at IFC “Caged Combat,” came in April 2006.
Number 6 » Sinosic vs. Ortiz