[3] Having not been selected in any NHL Entry Drafts, Bailey signed a two-year, entry-level contract with the Toronto Maple Leafs on March 21, 2015.

[7] Bailey played in his first NHL game on March 26, 2015, versus the Florida Panthers and was on the ice for the Maple Leafs lone goal in a 4–1 loss.

[9] During his first full professional season in 2015–16, Bailey was assigned to the Leafs' American Hockey League (AHL) affiliate, the Toronto Marlies, and produced 18 points in 38 contests before he was included alongside Dion Phaneuf in a nine-player trade to the Ottawa Senators organization on February 9, 2016.

[17] Following the conclusion of the camp with the Islanders, Bailey was not offered a contract but was reassigned to try-out with their AHL affiliate, the Bridgeport Sound Tigers on September 24, 2017.

[16] Unable to attract significant high-level North American interest, Bailey opted to take his career overseas, signing with HC Slovan Bratislava of the Kontinental Hockey League (KHL) on September 21, 2018.

Returning to North America as a free agent, Bailey was signed to a professional try-out (PTO) agreement with the Hershey Bears of the AHL on July 30, 2019.

On September 4, 2020, now a free agent from Växjö, Bailey remained in Europe, signing a one-year contract for the 2020–21 season with German club Iserlohn Roosters of the Deutsche Eishockey Liga (DEL).

[24] Following three seasons with Iserlohn, Bailey left the club after his contract and signed a one-year deal to continue in the DEL with ERC Ingolstadt on May 22, 2023.