2009-10: The fifth overall pick by Regina in the 2009 WHL Bantam Draft, Chandler Stephenson skated for the Saskatoon Contacts midget AAA team in the SMHL. He scored 17 goals with a team-leading 37 assists and had 34 penalty minutes in 42 games. The Contacts finished first in the regular season before falling to the Notre Dame Hounds in the playoff finals. Stephenson led all SMHL scorers in the playoffs with 5 goals and 14 assists in 11 games.
2010-11: Stephenson skated in 60 WHL games for Regina as a 16-year-old. He scored 7 goals with 12 assists and was minus-20 with 6 penalty minutes on a Pats team that missed the WHL playoffs after finishing fifth in the East Division. Stephenson played for Canada Western in the 2011 U17 World Hockey Challenge. In five games he scored 4 goals with 2 assists and had 8 penalty minutes.
2011-12: Stephenson was the fourth-leading scorer for the much-improved Pats – despite missing 14 games in the second half of the season due to a sprained knee. In 55 games he scored 22 goals with 20 assists and was minus-one with 24 penalty minutes. Under first-year coach Pat Conacher, Regina finished one point out of second in the East Division and reached the WHL playoffs. In the five-game playoff series with East champion Moose Jaw, Stephenson scored 1 goal with 3 assists and was plus-four. Stephenson was invited to the NHL Draft Combine and was ranked 33rd amongst North American skaters in Central Scouting's final rankings prior to the 2012 NHL Draft.
Stephenson has the skill, speed, and smarts to be a good offensive threat. He does lack the ideal size, however, at least in terms of his body mass. If he can overcome this deficiency, then he could be an effective, two-way performer in the NHL down the road.