Early career

Building on his impressive senior year at Center Grove, Bailey entered Division III Maranatha Baptist Bible College in Wisconsin where he continued to thrive on the mats, earning All-Conference three times and being named NCAA National Qualifier. The Church Ministries major returned to Indianapolis after graduation and began to train with Jake O'Brien and Chris Lytle to stay active as he mulled over an offer to move to Colorado Springs to train at the Olympic Training Center with the World Team training camp. Bailey began to feel more comfortable in the sport and decided to decline the invitation in order to pursue mixed martial arts and soon after, in 2006, Bailey had his first professional fight, a first-round TKO victory over Jason Cook.

For the past four years, Bailey has trained with Integrated Fighting Academy while also working part-time for the Indianapolis Fire Department with Chris Lytle. During this time, he has earned notable victories over John Kolosci and Waachiim Spiritwolf.^[1]

Strikeforce

Bailey made his Strikeforce on November 7, 2009, when he faced John Kolosci at Strikeforce: Fedor vs. Rogers.^[4] He won his debut via unanimous decision. Bailey then replaced an injured Bryan Travers, as he fought Justin Wilcox at Strikeforce Challengers 7 on March 26, 2010.^[5] He lost via unanimous decision and was subsequently released.

The Ultimate Fighter

In 2011, it was announced that Bailey had signed with the UFC to compete in The Ultimate Fighter: Team Lesnar vs. Team dos Santos.

Bailey was picked first on Team dos Santos and second overall. In the first preliminary bout of the season, Bailey was selected to fight Nordin Asrih. Bailey used his wrestling to control Asrih on the ground and win a clear-cut decision.^[6]

In the quarterfinals, he fought Chris Cope but lost via unanimous decision after two rounds. After the fight Shamar was visibly upset with the decision, saying numerous times, "he fought well, but not that good".^[7]

Ultimate Fighting Championship

Even though he lost in the quarterfinals, Bailey remained signed after the show. He made his official UFC debut June 4, 2011 on The Ultimate Fighter 13 Finale card, fighting against fellow quarterfinalist and teammate, Ryan McGillivray.^[8] He won the fight via unanimous decision.^[9]

Bailey dropped to Lightweight in order to face Evan Dunham at UFC Fight Night 25.^[10] He lost the fight via unanimous decision.

Bailey faced Danny Castillo on November 19, 2011 at UFC 139.^[11] During the official weigh ins, Bailey failed to make the weight limit for the Lightweight division. Bailey came in three pounds over, which resulted being fined 20 percent of his earnings, and the bout took place at a Catchweight of 158 lb.^[12] He lost the fight via TKO in the first round.^[13] After the loss to Castillo, Bailey was released from the promotion.^[14]

Post UFC

Bailey was scheduled to face UFC veteran Karo Parisyan at ShoFight 20 on June 16, 2012 for the vacant ShoFight Welterweight Championship. However, due to a medical suspension, Bailey was pulled from the fight and replaced by John Gunderson^[15]

Xtreme Fighting Championships

Bailey faced Bellator veteran Luis Santos at XFC 23 on April 19, 2013.^[16] He lost the fight via TKO at just over a minute into the first round.^[17]

Retirement

On October 7, 2014, Bailey announced his retirement from MMA competition.^[18]