Miles was drafted by Hawthorn with their second selection and forty-ninth overall in the 2014 national draft.[2] In 2016, Miles played 15 matches in the Victorian Football League (VFL) for the Box Hill before a broken collarbone late in the season ended his year.[3] After two years in the AFL, he made his debut in the twenty-four point loss to Adelaide at the Melbourne Cricket Ground in round 2, 2017.[4]
In 2018 he played the last eight games of the regular season only to be dropped for the finals campaign. He returned to Box Hill where he was an important member of the VFL premiership side.
He was delisted by Hawthorn at end of the 2019 AFL season.