Undrafted, Benn suited up with the Dallas Stars alongside his brother Jamie for a number of seasons. He was moved to Montreal, before continuing his tour of the northernmost NHL clubs with stops in Vancouver, Winnipeg and Minnesota, before ultimately concluding his stay with the Toronto Maple Leafs.
The rugged blueliner came to Winnipeg via Vancouver at the end of the 2021-22 season. He only suited up in eight games as a backup defensive option, but he did manage to register an assist and two penalty minutes. He put up the same stat line in three postseason games for the Jets that spring as well.