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 the Central Scouting final rankings. He was chosen by Washington in the third round (77th overall) in the 2012 NHL Draft.
2012-13: Stephenson played 46 regular season games for Regina in his third WHL season – missing 26 games due to a foot injury. He scored 14 goals with 31 assists and was -1 with 37 penalty minutes. The Pats missed the playoffs after finishing fifth in the East Division.
2013-14: Stephenson signed a three-year entry-level contract with Washington in April 2014 and made his pro hockey debut with Capitals AHL affiliate Hershey following his junior season with Regina. He scored his first professional goal and was +2 with no penalty minutes in two regular season games for the Bears. Stephenson scored 30 goals with 59 assists, both career highs, in his fourth WHL season with the Pats and was +27 with 65 penalty minutes. Regina finished first in the East Division before being swept by Brandon in a first round playoff series. Stephenson had 4 assists and was -3 with no penalty minutes in four playoff games.
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 he could be an effective, two-way performer in the NHL down the road.
Stephenson attended training camp with Washington before being assigned to AHL affiliate Hershey at the start of the 2014-15 season. The Bears have been one of the league's top teams with several minor league veterans. As a result Stephenson has struggled to find a permanent spot in the lineup as a 20-year-old first-year pro. He will likely see a more prominent role as he gains experience and adds the strength and bulk to compete at the pro level. Long term Stephenson looks like a fringe top-six player with the correct offensive abilities but not quite enough to standout. He is equally likely to top out as a top AHL player or head to Europe where his size would be less of an impediment to success.