2009-10: Trevor Cheek, who hails from Vancouver, Washington in the Portland area, skated for the Arizona-based PF Changs U18 team in the Midwest Elite Hockey League. In 48 games he scored 36 goals with 24 assists and had 62 penalty minutes.
2010-11: Cheek made the Calgary Hitmen in training camp as an 18-year-old in what was a rebuilding year for the defending WHL champions. In 57 games he scored 10 goals with 15 assists and was -15 with 37 penalty minutes. One year after finishing with the league's best record, the HItmen were last in the Central Division; winning a league-low 20 games.
2011-12: Cheek attended the San Jose Sharks' training camp before returning to Calgary for his second season in the WHL. He scored 23 goals with 26 assists in 67 games and was +6 with 75 penalty minutes. The much-improved Hitmen made the playoffs after finishing second in the Central Division. Cheek scored 3 goals with 1 assist and was -2 with 4 penalty minutes in the five-game series with Brandon.
2012-13: Cheek participated in Carolina's development camp before returning to Calgary and ended up playing for three WHL teams in his overage season. He played one game with Calgary before being traded to the Vancouver Giants in September and was obtained by the Edmonton Oil Kings in January at the WHL trade deadline. In 71 regular season games between the three teams he scored 32 goals with 28 assists and was +12 with 57 penalty minutes. Edmonton finished first in the Central Division and advanced to the WHL finals against the Portland Winterhawks. Cheek played 15 playoff games and had 8 goals with 8 assists, finishing +17 with 14 penalty minutes, but missed the final series against his hometown Winterhawks due to an undisclosed injury he suffered in the Eastern Conference finals against Calgary. Cheek signed a three-year entry-level contract with Colorado in April, 2013.
Cheek signed an entry-level contract with the Colorado Avalanche in April of 2013.