Bailey played for the Alaska Anchorage Seawolves in the NCAA Men's Division I Western Collegiate Hockey Association (WCHA).

[4] As a free agent, Bailey belatedly signed to a one-year AHL contract with the Stockton Heat, the primary affiliate to the Calgary Flames on September 6, 2016.

[5] In the 2016–17 season, Bailey split between the Flames' AHL and ECHL affiliates, appearing in 17 games for 7 points with the Heat before opting to sign his first contract abroad in agreeing to join Swedish second division club, Mora IK in their upcoming playoff quest on February 10, 2017.

On July 22, 2019, Bailey agreed to a one-year contract with German club, ERC Ingolstadt of the Deutsche Eishockey Liga (DEL).

With the COVID-19 pandemic ending the DEL season before the playoffs, Bailey left the club as a free agent to return to the Swedish Allsvenskan by agreeing to a one-year contract with Södertälje SK on June 12, 2020.