 After playing minor hockey with the Saskatoon Redwings (and figure skating out of Martensville and Saskatoon Figure Skating Club, coached by his mother Rosemary), Armstrong left to play Midget AAA with the Yorkton Mallers, where he scored 44 goals and 77 points in 40 games, finishing 3rd in league scoring.Armstrong began playing for the Kootenay Ice of the Western Hockey League (WHL) in the 2002–03 season, scoring 6 goals.He was then traded to the Everett Silvertips during the 2003–04 season, scoring 18 goals.