After the 2010–11 season with the Texas Stars of the AHL, Benn signed his first NHL contract in agreeing to a one-year, two-way deal with the Dallas Stars on July 2, 2011.[3] In the following 2011–12 season, on January 3, 2012, Benn made his NHL debut against the Detroit Red Wings. He recorded his first NHL point, also assisted on by his brother Jamie, on a goal by Loui Eriksson.[4] As an impending free agent following the 2015–16 season, Benn opted to remain with the Stars, signing a three-year, $3.3 million contract on June 24, 2016.[5]
Montreal Canadiens
In the midst of the 2016–17 season, Benn's tenure with the Stars came to an end after seven years, as he was traded prior to the deadline to the Montreal Canadiens in exchange for Greg Pateryn and a fourth-round draft pick in 2017 on February 27, 2017.[6] On March 4, 2017, Benn scored his first goal with the Canadiens in a 4–1 victory against New York Rangers in Madison Square Garden.[7]
When playing against his former team the following season against his brother, Benn said:
Obviously there's a bit of a shadow when your brother [Jamie Benn] is the superstar of the Stars," Benn said on Tuesday morning. "I never thought about it like that but obviously everybody could see it. It was nice to get away and just play my game and be myself.[8]
Vancouver Canucks
On July 1, 2019, Benn returned to his home province, signing as a free agent to a two-year, $4 million contract with the Vancouver Canucks.[9] On February 10, 2020, Benn scored his first goal with the Canucks in a 6–2 win over the Nashville Predators.[10]
Winnipeg Jets
In his final year under contract with the Canucks in the 2020–21 season, Benn was dealt at the trade deadline to the Winnipeg Jets for a 2021 sixth-round pick on April 12, 2021.[11] In the closing stages of the regular season Benn, was competing with Logan Stanley and Ville Heinola for playing time, registering one assist through eight games.[12][13] He featured in three playoff contests with the Jets, before ending his tenure with the club following a second-round series defeat to the Montreal Canadiens.[14]
Minnesota Wild
As a free agent, Benn signed a one-year, $900,000 contract to join his fifth NHL club, the Minnesota Wild, on August 27, 2021.[15] Benn played in 39 games registering one goal and 8 points.[16]
Toronto Maple Leafs
Again a free agent the following off-season, Benn continued his NHL journey by signing a one-year, $750,000 contract with the Toronto Maple Leafs on July 14, 2022, the second day of free agency.[17] After missing time with a groin injury, Benn played in his first game with the Maple Leafs on November 12, scoring his first goal with the team.[18][19] On November 23, Benn suffered an upper-body injury in a 2–1 win over the New Jersey Devils.[20] He returned from injury on December 12[21] and made the starting lineup on December 27, 2022.[22] On February 25, 2023, Benn was placed on waivers for the purpose of sending him to the Maple Leafs AHL affiliate, the Toronto Marlies.[23] He finished the season playing in 12 games for the Maple Leafs, registering two points and 23 games for the Marlies, recording six points.[24]
Brynäs IF and retirement
As an unrestricted free agent with the completion of his contract with the Maple Leafs, on August 30, 2023, Benn agreed to a professional tryout contract with returning to the Dallas Stars organization for their 2023 training camp, but he was unsuccessful in obtaining a roster slot for the 2023–24 season.[24] He then signed a one-year contract with Brynäs IF of the second-tier Swedish league, HockeyAllsvenskan, on October 14, 2023.[25] Following the 2023–24 season, where Brynäs IF managed to secure promotion, after winning in the playoffs, Benn announced his retirement on September 10, 2024.[26]