2007-08: Dylan Olsen played for the Camrose Kodiaks of the AJHL. He appeared in 49 games for the Kodiaks, scoring eight goals and 16 assists while picking up 45 penalty minutes. Olsen was a driving force in the Kodiaks championship season.
2008-09: Olsen again played for the AJHL's Camrose Kodiaks. In 53 games for that club, he scored 10 goals and added 19 assists while racking up 123 penalty minutes. Olsen also played for Team Canada West in the 2008 World Junior A Challenge, picking up one goal and four assists in five games. In addition, he starred for Team Canada at the Under-18 World Junior Championships, scoring two goals and two assists while adding 14 penalty minutes in six games. Olsen was chosen in the first round, 28th overall, of the 2009 NHL Draft by the Chicago Blackhawks.
2009-10: As a freshman at the University of Minnesota-Duluth, Olsen skated in 35 games and eventually ascended to the Bulldogs' top defensive pairing. He scored 1 goal and 10 assists for 11 points in his first year while earning 47 PIMs. Olsen was one of the final cuts from Canada's U20 WJC camp.
2010-11: Olsen got off to strong start on the ice with the University of Minnesota-Duluth, scoring 1 goal, 12 assists for 13 points in 17 games as part of the Bulldog's formidable top pairing with Justin Faulk (CAR). Olsen then earned a spot on Canada's WJC team, where he also played a lot of top pairing minutes but scored just 2 assists in 7 games for the silver medal winning team. He was signed to an entry-level contract during the WJC tournament due to being ruled academically ineligible at Duluth. He was forced into the Rockford lineup and played 42 AHL games with 4 assists and a minus-18 rating in his first taste of pro hockey.
2011-12: Olsen made his NHL debut in January and saw significant action in 28 games as the Blackhawks defense corps was beset by injuries. In 28 games with Chicago he was minus-five with 1 assist and 6 penalty minutes. Olsen played in one playoff game during the Blackhawks' six-game series with Phoenix – seeing just under five minutes of ice time. He skated in 44 AHL games with Rockford prior to being called up and was minus-five with 4 goals and 3 assists and 44 penalty minutes.
2012-13: Olsen spent the entire season back in the AHL with Chicago affiliate Rockford after skating in 28 games for the Blackhawks in 2011-12. A healthy scratch at times early in the season, Olsen scored 2 goals with 9 assists and was -4 with 27 penalty minutes in 50 games for the IceHogs. Rockford finished third in the Midwest Division, two points behind Milwaukee for the final Western Conference playoff spot.
Olsen is a defenseman with decent size who projects as a defensive-first blueliner at the NHL level. He skates well for a big man and has a good top end speed. His heavy, accurate shot is effective on the man advantage, but he will need to continue developing his offensive instincts to play a consistent role on the power play in the NHL. He is a capable puck mover but is still prone to making bad decisions with the puck. Defensively, Olsen can use his size and strength to knock forwards off the puck. His footwork and quickness could still use some work and he needs to be more active in the play to make his presence felt.
From skating in 25 NHL in the 2011-12 season to a limited role in Rockford through much of 2012-13, it is safe to say that Olsen has fallen out of favor to some extent among the Blackhawks blue line prospects. The 2013-14 season will be important for him, as there will be plenty of competition for minutes in Rockford with the likes of Ryan Stanton and Klas Dahlbeck playing similar stay-at-home games.
Olsen was dealt by the Chicago Blackhawks along with Jimmy Hayes to the Florida Panthers in the deal that brought Kris Versteeg back to the Blackhawks.