Bailey scored the game-winning goal in his 1,000th NHL game when the New York Islanders defeated the Carolina Hurricanes 6-2 at PNC Arena in Raleigh, North Carolina, on Oct. 28, 2022. He gave the Islanders a 3-2 lead at 16:26 of the third period when he took a pass from Mathew Barzal, drew goalie Frederik Andersen out of position and scored on the backhand to become the third skater to play 1,000 games with New York, joining Hall of Famers Denis Potvin (1,060) and Bryan Trottier (1,123).

Bailey's long tenure with the Islanders ended when he and a second-round pick in the 2026 NHL Draft were traded to the Chicago Blackhawks for future considerations June 29, 2023, and then put on waivers for the purpose of a buyout. He was selected by the Islanders with the No. 9 pick at the 2008 NHL Draft after he scored 96 points (29 goals, 67 assists) in 67 games with Windsor of the Ontario Hockey League.

He made the NHL roster out of training camp as an 18-year-old and signed a three-year, entry-level contract with New York on Oct. 3, 2008. In 68 games as a rookie with the Islanders, he scored 25 points (seven goals, 18 assists), including his first NHL goal against the Phoenix Coyotes on Jan. 2, 2009.

Bailey increased his totals to 16 goals and 35 points in 73 games during his second season and got his first taste of the Stanley Cup Playoffs in the shortened 2012-13 season, when he scored 19 points (11 goals, eight assists) in 38 regular-season games and three assists during a six-game loss to the Pittsburgh Penguins in the first round.

In 2014-15, Bailey had 15 goals and 41 points, then scored two goals and five points in a seven-game loss to the Washington Capitals in the Eastern Conference First Round. He scored 32 points (12 goals, 20 assists) in 81 games in 2015-16 when New York advanced to the second round of the playoffs for the first time since 1993 by defeating the Florida Panthers in six games. Bailey finished that postseason with three points (two goals, one assist) in nine games.

He had 56 points in 2016-17 (13 goals, 43 assists), then became an All-Star for the first time the following season with an NHL career-high 71 points (18 goals, 53 assists) in 76 games. On Dec. 14, 2017, Bailey had his first NHL hat trick in a 6-4 loss to the Columbus Blue Jackets.

Bailey once again helped the Islanders reach the second round of the playoffs in 2018-19, scoring 56 points (16 goals, 40 assists) in 82 regular-season games and six points (four goals, two assists) in eight playoff games, including an overtime goal against the Penguins in Game 1 of the first round.

He had 43 points (14 goals, 29 assists) in 68 games when the 2019-20 season was paused March 12 due to concerns surrounding the coronavirus.