Cheek was the United States Air Forceboxing champion[4] and started training in kickboxing and Muay Thai in 2000 at the age of twenty-three. In August 2004, he competed in a four-man tournament held over two days in Orlando, Florida to determine the IKF Amateur North American Super Heavyweight (+106.8kg/235lb) Muay Thai Champion. After defeating Bernard Settle, Jr. by technical knockout in round two of their semi-final bout, he outpointed Brian Wells to a unanimous decision in the final to take the crown.[5] He followed this up with the IKF's Amateur California Muay Thai title when he stopped Ben Davis with low kicks in round one in Fairfield, California on March 26, 2005.[6]
After turning professional, Cheek made his K-1 debut on August 13, 2005, in a tournament reserve bout at the K-1 World Grand Prix 2005 in Las Vegas II against Mike Sheppard, knocking him out in the second round.[7] He was absent from both K-1 Las Vegas events in 2006 due to a torn ACL and MCL he sustained in February 2006.[4]
After a year out of the ring, Cheek returned on August 11, 2007, for the K-1 World Grand Prix 2007 in Las Vegas tournament. He stopped Imani Lee with a barrage of unanswered punches in round three in the quarter-finals but was unable to continue in the tournament due to a leg injury and was replaced by Doug Viney, who eventually went on to win the title.[8][9]
In early 2008, Cheek fought for the Miami Force in the World Combat League and, on June 20, 2008, faced Patrice Quarteron for the vacant IKF World Super Heavyweight (+106.8kg/235lb) Muay Thai title in Montego Bay, Jamaica. He was sent to the canvas early with a flurry of punches and elbows. After beating the count, he was dropped with a low kick, which also caused Quarteron to fall over. As both fighters fell to the canvas, Quarteron's knee landed on Cheek's head, seemingly knocking him unconscious.[10]
He soon made his way back to K-1 to fight in the K-1 World Grand Prix 2008 in Hawaii in Honolulu on August 9, 2008. He won by TKO against Kyokushin karate stylist Nicholas Pettas in the quarter-finals when Pettas aggravated a groin injury sustained in training early in the fight. He was then eliminated by the eventual tournament winner Gökhan Saki in the semis. He was floored with low kicks before being crumpled with a liver punch towards the end of round one.[11][12][13]
On August 28, 2010, Cheek lost to Steven Banks via second-round KO in a fight for the WBC Muaythai United States Super Heavyweight (+104.5kg/230lb) title. He struggled with the knees of Banks, being floored by them on four occasions throughout the match.[15]
Cheek suffered a one-sided beating at the hands of Cătălin Moroşanu, after re-tearing his MCL in the first round in their SuperKombat World Grand Prix 7 in Varna, Bulgaria bout on July 7, 2012. He was dropped five times, forcing referee Cezar Gheorghe to call a halt to the bout in the second round.[16]
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