2007-08: Matt Bailey played for the Neepawa Natives in the Manitoba Junior Hockey League and skated for Canada Western in the 2008 U17 World Hockey Challenge. He scored 13 goals with 15 assists and 63 penalty minutes in 56 MJHL games. Bailey played four games and had no points and 2 penalty minutes at the WHC as Canada Western captured a bronze medal.
2008-09: Bailey skated for the Tri-City Storm in his first USHL season. He scored 10 goals with 14 assists and was -31 with 49 penalty minutes in 58 games. The Storm had the league's worst record. Bailey committed to playing college hockey at Alaska-Anchorage in 2010-11.
2009-10: Bailey went from Tri-City to Sioux Falls in his second USHL season. He was the Stampede's third-leading scorer, finishing with 14 goals and 33 assists, and was +11 with 69 penalty minutes in 59 regular season games. Sioux Falls finished third in the Western Division before being swept by second-place Fargo in a three-game playoff series. Bailley had 2 goals and was +2 with 2 penalty minutes in three playoff games.
2010-11: Bailey skated in 30 of 37 games for the University of Alaska-Anchorage in his freshman season. He was the Seawolves fourth-leading scorer with 10 goals and 10 assists and was an even plus-minus with 23 penalty minutes. Alaska-Anchorage finished eighth in the WCHA; sweeping Minnesota in a first round series before falling to Colorado College in the Final Five.
2011-12: Bailey led Alaska-Anchorage with 10 goals in a disappointing season as the Seawolves slipped to last place in the WCHA; winning nine games all season. The sophomore had 7 assists and was -11 with 30 penalty minutes in 34 games.
2012-13: Bailey scored 7 goals with 12 assists in 36 games in his junior season at Alaska-Anchorage; leading the Seawolves with 65 penalty minutes and finishing -19. After defeating St. Cloud State on Dec. 1st to raise its record to 3-5-4, Alaska-Anchorage won just one more game, on February 8th against Michigan Tech, and finished last in the WCHA.
2013-14: Bailey was the leading scorer for Alaska-Anchorage as the Seawolves under first-year coach Matt Thomas finished the regular season with a winning record for the first time since 1992-93. Bailey scored 20 goals with 18 assists and was +15 with 49 penalty minutes in 38 games. After finishing sixth in the re-aligned 10-team WCHA, the Seawolves overcame an overtime loss in Game 1 of their series against Alaska-Fairbanks to take their three-game series and then took league champion Ferris State to overtime in the WCHA semifinals before falling 5-4. Bailey signed a two-year, entry-level contract with Anaheim as a free agent on March 26th, 2014.
Anaheim signed Bailey to a two-year entry-level contract on March 26th, 2014.