While playing with Richmond's reserves side in 2018 he won the J.J. Liston Trophy as the Victorian Football League's best and fairest player.

He signed his first contract with the club while still in high school in June 2010, opting out of a potential nomination for the AFL draft in the process.

[11] He didn't miss another game that season, including appearing in the club's losing elimination final to Port Adelaide.

[23] In round 19 he recorded his lowest disposal match since joining Richmond, picking up just 11 during his side's huge loss to his old club Greater Western Sydney.

[26] As with the previous season, Miles' 2017 pre-season saw him training to improve his aerobic fitness in addition to adding versatility to his game.

[27] But with the off-season addition of Josh Caddy and Dion Prestia, Miles was squeezed out of the Richmond midfield brigade, forced to sit out the season opening match for the first time in three years.

[30] Richmond VFL coach Craig McRae referred to Miles as "an AFL player waiting for an opportunity" after he recorded 35 disposals and two goals in one such match.

[31] He made his return to AFL football in round 7, called to the senior side to play the reigning premier Western Bulldogs.

[33] Miles returned once more for a single game in round 9, this time recording 15 disposals, one tackle and two marks in the loss to his former team the GWS Giants.

[34] After being dropped for round 10, another two months of VFL football awaited, where he was a consistent performer including a three week run of 35, 34 and 32 disposals.

[35] In round 17 he once more returned to senior football, recording 24 disposals, eight marks and four tackles in Richmond's win over the Brisbane Lions.

[46] Miles underwent minor shoulder surgery in the 2017/18 off-season, allowing him to focus on building aerobic fitness and reducing his weight before returning to contact drills in February.

[47][48] The early part of the 2018 season, however, followed much the same story as the previous year, with Miles playing consistently "above VFL level" in Richmond's reserves side.

[51][52] At the lower level he was subjected to weekly tagging that lead to significant back stress and soreness, the result of which saw him rested for one match in late May.

[53] Upon his return, he logged a magnificent game, including recording 44 disposals, 11 marks, 12 clearances and kicking three goals in a VFL win over the Collingwood reserves.

[55] He recorded 20 disposals and kicked a goal in that Round 12 loss to Port Adelaide before being immediately dropped back to VFL level following Martin's return.

[6] By the last week of the AFL home-and=away season, media reports had begun to emerge linking Miles to a trade deal with Gold Coast.

[64] Richmond football boss Neil Balme publicly confirmed the reports just three days out from the start of the trade period and suggested the club would seek little in return for the pair's departure.

[70] Miles, along with former teammates Dustin Martin, Reece Conca, Dion Prestia, Toby Nankervis and Josh Caddy, owns a small stake in racehorse Main Stage which ran in the 2017 spring racing carnival.