#1 Ken Shamrock
Ken Shamrock has won MMA tournaments. However, the UFC Hall of Famer never won in UFC, the company which made him famous.
Shamrock has worked for many MMA and pro-wrestling promotions over the past three decades, but UFC is where he is still most closely associated.
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It is somewhat surprising then, that despite competing in several UFC tournaments, this pioneer of MMA never won one.
He competed in UFC 1 and made light work of Pat Smith in the first round before submitting to the eventual winner, Royce Gracie in the Semi-Final. Shamrock by his own admittance had taken the smaller Gracie for granted. Eager to avenge his defeat, the "World's Most Dangerous Man" as he would become known signed up to UFC 2, but had to withdraw due to injury. UFC 3 was promoted around Shamrock and Gracie and the pair were separated in the brackets in the hopes that both would make it to the final.
Neither did.
Gracie was so exhausted after his first round victory over Kimo Leopoldo that he could not compete in his Semi-Final bout. Shamrock defeated Christophe Leininger and Felix Mitchell to advance to the Final, but when Gracie withdrew, so did he. Shamrock had little interest in fighting anyone other than the Brazilian in the Final. Given he had also suffered a hand injury in the previous round, Shamrock had no desire to contest the Championship fight. However, this would be the closest he would ever come to winning a UFC tournament.
Shamrock became the first UFC Superfight Champion at UFC VI and would not compete in another tournament until the Ultimate Ultimate 1996, which turned out to be his final UFC appearance for six years, when he defeated Brian Johnstone in round one, but was forced to withdraw through injury once more.
Shamrock is perhaps the most famous MMA superstar ever who never won a UFC tournament title.