Bowles was born in Charleston, West Virginia and raised in the small town of Chesapeake, West Virginia by his single mother. Bowles' father, who was largely absent from his life, died when Bowles was 11 years old. In the eighth grade, Bowles moved to Jackson County, Georgia, attending Jackson County Comprehensive High School where competing in wrestling for three years. Bowles was later introduced to mixed martial arts by a former teammate after graduating, and began training at The HardCore Gym.
Bowles compiled an undefeated 7-0 amateur record and began his professional career in regional promotions, earning two first-round stoppages and amassing an undefeated record of 3-0.
In his first two fights in the organization, he submitted Charlie Valencia with a rear-naked choke and knocked out Marcos Galvao at WEC 31 with a flurry that stunned his opponent and a strong right hook to finish, both ending within minutes of the second round, showcasing his proficiency in striking and submission offense (with a primarily wrestling base).
At WEC 35 he finished fellow Bantamweight contender Damacio Page with an impressive first-round guillotine choke he locked in while his opponent was still standing. It was near the end of 2008 where Bowles would have his most notable victory in the organization yet, defeating Will Ribeiro (who was 10-1 at that time) in the third round via another guillotine choke, on the WEC 37 main card. He was then scheduled to headline WEC 40 in a bout with Miguel Torres, but was forced to withdraw due to a back injury weeks before the event, and was replaced by top ten bantamweight Takeya Mizugaki. Torres successfully defended his belt against Mizugaki.
Torres and Bowles headlined WEC 42 on August 9, 2009 at the Hard Rock Hotel and Casino in Las Vegas, Nevada. Bowles defeated Torres via first-round KO to become the new WEC Bantamweight Champion.
Bowles made his first title defense against Dominick Cruz on March 6, 2010 at WEC 47. Bowles lost via TKO (doctor stoppage) at the end of the second round with a broken hand.
Bowles was expected to face Wagnney Fabiano at on November 11, 2010 at WEC 52. However, Bowles was forced off the card with a foot injury.
On October 28, 2010, World Extreme Cagefighting merged with the Ultimate Fighting Championship. As part of the merger, all WEC fighters were transferred to the UFC.
Bowles faced former opponent Damacio Page on March 3, 2011 at UFC Live: Sanchez vs. Kampmann. In what Joe Rogan described as " a comet that comes around every 1,000 years," Bowles defeated Page by guillotine choke at 3:30 of the first round, the same method and exact time that he defeated Page in their first meeting.
Bowles faced Takeya Mizugaki on July 2, 2011 at UFC 132. He won the fight via unanimous decision (30–27, 30–27, and 29–28), making this the first time he has gone to a decision in his career.
Bowles faced off against Urijah Faber on November 19, 2011 at UFC 139. He lost the fight by submission (guillotine choke) in the second round.
Bowles returned from an extended 18-month layoff and faced George Roop on May 25, 2013 at UFC 160. He lost the fight via TKO in the second round.
Bowles failed his UFC 160 drug test with an elevated testosterone-to-epitestosterone (T/E) ratio. The NSAC allows a T/E Ratio of 6:1 and Bowles was over 20:1. Bowles did not appeal the result and was subsequently suspended for nine months and fined $5,700.
Bowles was released from the UFC on March 2, 2015.
On January 14, 2015 Bowles along with Rhomney Marie Moon were arrested and face multiple felony charges in Arcade, Georgia.World Extreme Cagefighting
WEC Bantamweight Championship (One time)
Knockout of the Night (One time)
Submission of the Night (Two times)
Ultimate Fighting Championship
Submission of the Night (One time)