At the conclusion of his entry-level contract with the Ducks, Bailey was not tendered a qualifying offer in order to retain his rights on June 27, 2016.[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.[6]
After spending two full seasons in the Swedish Hockey League with Mora IK, Bailey left as a free agent following their return to the Allsvenskan at the conclusion of the 2018–19 season. On July 22, 2019, Bailey agreed to a one-year contract with German club, ERC Ingolstadt of the Deutsche Eishockey Liga (DEL).[7] In the 2019–20 season, Bailey adapted quickly with ERC by registering 9 goals and 25 points through 48 regular season games.
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.[8]