2009-10: Jaynen Rissling played in 36 WHL games for the Calgary HItmen as a 16-year-old. He had 8 assists and was plus-seven with 19 penalty minutes. Calgary finished with the league's best record and reached the Memorial Cup after winning the league playoff title. Rissling appeared in nine of 23 playoff games and was plus-seven; scoring 1 goal with 2 assists and 4 penalty minutes. Rissling dressed in one game during the Memorial Cup and had no points or penalty minutes. Calgary lost 5-4 in overtime to WHL rival and tournament host Brandon in the semifinal game.
2010-11: Rissling skated in 67 of 72 games for the HItmen in his second WHL season. Rissling's minus-27 plus/minus was indicative of playing substantial minutes on a team that won just 20 games and had the league's worst record. He scored 5 goals with 16 assists and was second on the team with 95 penalty minutes.
2011-12: Rissling was a physical force on the blue line for the Hitmen while contributing offensively. In 55 games he scored 5 goals with 18 assists and was plus-nine with a team-high 124 penalty minutes. Calgary returned to the top of the WHL standings, finishing second behind the Edmonton Oil Kings. In the five-game playoff series with Brandon, Rissling was minus-five with no points or penalty minutes. Ranked 135th amongst North American skaters in Central Scouting's final rankings, Rissling was selected by Washington in the seventh round (197th overall) of the 2012 NHL Draft.