Garland was born on March 11, 1996, in Scituate, Massachusetts,[1] to parents Bridget, a train station foreman, and Garry, who was a collegiate ice hockey player.

[5] After beginning the 2012–13 season with the Muskegon Lumberjacks of the United States Hockey League (USHL), Garland moved to playing for the Wildcats in the QMJHL, foregoing his NCAA eligibility.

[5][6] During the 2014–15 season, while playing with the Wildcats, Garland led both the QMJHL and Canadian Hockey League (CHL) with 129 points.

While in his final season of junior level with the Wildcats, Garland was signed to a three-year, entry-level contract by the Coyotes on December 23, 2015.

[8] Following the conclusion of the season, Garland was invited to participate in the Coyotes' 2016 development camp,[9] and remained in the state for the remainder of the off-season.

[10] Following camp, Garland was reassigned to the Coyotes' American Hockey League (AHL) affiliate, the Tucson Roadrunners, for the 2016–17 season.

Having established a role within the Coyotes, adding 12 goals in 35 games, Garland was signed to a two-year, $1.55 million contract extension on February 27, 2019.

[17] During a game against the Calgary Flames, Garland suffered a lower-body injury when he collided with goaltender Cam Talbot.

[21] On June 9, Garland was the Coyotes' nominee for the Bill Masterton Memorial Trophy as a "player who best exemplifies the qualities of perseverance, sportsmanship, and dedication to hockey.