Buffalo Sabres

Bailey was selected by his hometown team, the Buffalo Sabres in the 2nd round (52nd overall) of the 2013 NHL Entry Draft.^[6]

Bailey signed a three-year entry-level contract with the Sabres on November 2, 2014.^[7] He was recalled to the Sabres from the American Hockey League's Rochester Americans on February 10, 2016, and made his NHL debut on February 11.^[8] He was reassigned to Rochester on February 18,^[9] only to be recalled again three days later following an injury to Ryan O'Reilly.^[10] He scored his first NHL goal on January 3, 2017, against Henrik Lundqvist and the New York Rangers.^[11]

During the 2017–18 season, Bailey was suspended one game for a high hit on Reid McNeil during a game against the Syracuse Crunch in March. However, he was called up to the NHL on March 14, 2018, a day before he was set to serve his suspension.^[12] He was set to serve his suspension once he is sent back to the AHL.^[12] He was reassigned to the AHL on March 27, 2018, after playing in 5 games.^[13]

Philadelphia Flyers

The Sabres traded Bailey to the Philadelphia Flyers on January 17, 2019, in exchange for forward Taylor Leier.^[14] He was assigned to the Lehigh Valley Phantoms, the Flyers' AHL affiliate, playing on a line with Mikahil Vorobyev and Colin McDonald for the Flyers to assess whether there was a position for him in their NHL roster.^[15] He was recalled to the Flyers on February 10 under suspicion that, should Wayne Simmonds be traded as part of the February 25 trading deadline, Bailey would take his position in the roster.^[16] Even after Simmonds was traded to the Nashville Predators, however, Bailey struggled to remain in the Flyers lineup, and spent most of his time in Lehigh.^[17] Between February 10 and April 11, Bailey was sent either up or down between the two teams 10 times. His final recall came on March 20, and he finished out the season with the Flyers. Altogether, he played 11 games for Philadelphia and 17 for Lehigh Valley.^[18] The Flyers did not extend a qualifying offer to Bailey at the end of the season, making him an unrestricted free agent.^[19]

Vancouver Canucks

On July 4, 2019, Bailey signed to a one-year, two-way contract with the Vancouver Canucks.^[20]

On January 30, 2020, Bailey was called-up by the Vancouver Canucks from the Utica Comets following an injury to Tyler Motte.^[21] He appeared in two games^[22] prior to the pause of the 2019–20 season.^[23]

After playing just 3 games, Bailey was injured on February 11, 2021. The injury required surgery causing him to miss the remainder of the season.^[24]

Edmonton Oilers

As a free agent from the Canucks, Bailey failed to gain interest for an NHL contract before opting to sign a one-year AHL deal with the Bakersfield Condors on September 8, 2022.^[25] In the 2022–23 season, Bailey recorded 10 points through his first 16 games with the Condors leading him to sign a one-year, two-way contract with NHL affiliate, the Edmonton Oilers, on January 6, 2023.^[26] He remained with the Condors for the duration of his contract, posting 32 points through 58 regular season games.

San Jose Sharks

As a free agent at the conclusion of his contract with the Oilers, Bailey remained un-signed over the summer before joining the San Jose Sharks 2023 training camp. On October 12, 2023, he was signed by AHL affiliate, the San Jose Barracuda to a one-year contract.^[27] Adding 6 goals and 11 points through 16 games, for the second consecutive season, Bailey earned a NHL contract during the season, in signing a one-year, two-way contract with the Sharks on November 27, 2023.^[28] With the Sharks suffering a rash of injuries, Bailey was immediately recalled and made his Sharks debut on the same day, marking his return to the NHL by adding a primary assist on the game-winning goal of a 2–1 victory over the Washington Capitals.^[29]

Regular season and playoffs

International