Benson was signed by the Edmonton Eskimos on June 11, 2012. He was released by the Eskimos on June 17, 2012.[2] He signed with the Eskimos on October 18, 2012.[3]
Benson signed with the Toronto Argonauts on June 1, 2014. He was released by the Argonauts on June 22, 2014.[4]
Benson was signed by the BC Lions on August 31, 2014.[5] During his fourth year as the Lions' long snapper, Benson recovered a muffed punt that he had snapped and which Edmonton wideout Brandon Zylstra failed to secure. Benson returned the ball for a touchdown against his former team.[6] Benson received a one-year contract extension to remain with the Lions on January 11, 2018.[7] He played in all 18 games in 2018, but was released from BC during the following off-season on May 1, 2019. During six years in the CFL and 84 games played, Benson had accumulated 16 tackles on special teams.
Benson signed with the Ottawa Redblacks to a practice roster agreement on July 22, 2019.[8] Benson was called up when Ottawa's regular long snapper Louis-Philippe Bourassa was suspended for two games.[9] Benson also played the final three games of the season for Ottawa. He was released by the Redblacks on January 23, 2020.[10]
On January 27, 2020, it was announced that Benson had signed a one-year contract with the Montreal Alouettes.[11] However, the 2020 CFL season was cancelled and he did not play for the Alouettes.
Upon entering free agency, Benson signed with his hometown Winnipeg Blue Bombers on February 9, 2021.[12] He played in all 14 regular season games and both post-season games in 2021 as he finished the season as a Grey Cup champion following the Blue Bombers' victory over the Hamilton Tiger-Cats in the 108th Grey Cup game.[13] For the following three seasons, he played in every regular season and post season game, including the team's three straight Grey Cup losses.[13]
In 2025, Benson was injured in the first game of the season and spent the following five games on the injured list.[14] With his replacement, Ian Leroux, playing well, Benson was a healthy scratch for two games and then was ultimately released on August 12, 2025.[14]
