Bailey began his professional baseball career with the Gulf Coast Reds and later advanced to the Class A Dayton Dragons. He was promoted the Class A Advanced Sarasota Reds and then the Class AA Chattanooga Lookouts. After appearing with the Reds in spring training, he was sent to the Class AAA Louisville Bats before finally debuting with the Reds.
On September 28, 2012, Bailey made history by becoming the 16th pitcher in Reds franchise history to toss a no-hitter in a game against the Pittsburgh Pirates at PNC Park. This was also the first no-hitter tossed within that stadium. In the game, Bailey allowed only two baserunners, one on a walk and one on an error. The final score was 1-0.
In December of 2018, he was traded to the Los Angeles Dodgers.
On February 9, 2019, he was traded to the Kansas City Royals.