After being named to the WHL West first All-Star team, Benn paced the Rockets with a playoff-leading 33 points en route to the 2009 Ed Chynoweth Cup title.

Although the Rockets lost to the Windsor Spitfires 4–1 in the Final, Benn was named to the Tournament All-Star team, along with teammate Tyler Myers.

He scored 14 goals, 12 assists and had 26 points in 24 playoffs games as Texas fell to the Hershey Bears in the Calder Cup Finals.

Benn later spoke of the experience, "I had a fun summer here...it was a big part of my hockey career and helped me develop my game.

[citation needed] With the 2012–13 season delayed due to the labour lock-out, Benn signed a contract for the duration of the dispute with the Hamburg Freezers of the German DEL on October 2, 2012.

His final point, a secondary assist on a goal by Cody Eakin with 8.5 seconds left in the game, allowed him to overtake New York Islanders forward and captain John Tavares for the award.

Benn was named a finalist for the Ted Lindsay Award as the most outstanding player which ultimately went to Montreal Canadiens goaltender Carey Price.

[21] On April 8, 2021, Benn recorded his 400th career NHL assist on a goal by Roope Hintz in a 5–1 win over the Chicago Blackhawks.

On December 11, 2023, Benn recorded his 500th NHL assist on a goal by Miro Heiskanen in a 6–3 win over the Detroit Red Wings.

[26] Benn would finish the 2023–24 season with 21 goals, 39 assists for 60 points in all 82 contests as the Stars as a team clinched the top seed in the Western Conference.

Playing in his second WHL season, Benn was named to Team Canada, along with Kelowna Rockets teammate Tyler Myers, for the 2009 World Junior Ice Hockey Championships in Ottawa.

He contributed 4 goals and 2 assists in 6 games, helping Canada to its record-tying fifth straight gold medal, defeating Sweden 5–1 in the final.

[30] He scored the only goal in a 1–0 win against the United States in the semi-final, to advance Canada to the gold medal game, where they eventually beat Sweden 3–0.