[3] Two days after his release, Miles signed with the Winnipeg Blue Bombers on March 4, 2017.
During the 2019 Winnipeg Blue Bombers season, Miles once again played in all 18 regular season games and both playoff games, where he recorded four defensive tackles and eight special teams tackles.
He was also featured as a long snapper for the first time in his professional career following an injury to Chad Rempel during the Labour Day Classic game.
[4] Miles played in his first Grey Cup game on November 24, 2019 and won his first championship following the Blue Bombers' victory over the Hamilton Tiger-Cats in the 107th Grey Cup game.
[5] The 2020 CFL season was later cancelled due to the COVID-19 pandemic, and Miles became a free agent afterwards.