[7] Stewart joined the Townsville Crocodiles for the start of the 2007–08 NBL season, where he played four games between 26 September and 11 October as an injury replacement.
[8][9] Stewart debuted in the South East Australian Basketball League (SEABL) in 1989 for Devonport (later known as NW Tasmania).
[24] The Huskies endured what was described as "shambolic" away trips across the Tasman during the 2019 New Zealand NBL season which strained relationships between staff and players, only some of whom were being paid on time.
[26] Stewart was set to return to the Hobart Chargers for the 2020 NBL1 season but the team ultimately missed the entire year due to the COVID-19 pandemic.
[27] He made his return as Chargers head coach in the NBL1 South in the 2021 season,[28] guiding the team to a third-place finish with an 11–4 record.
[29] He re-signed for the 2022 season[29] and led the Chargers to the NBL1 South championship after they defeated the Mount Gambier Pioneers in the grand final.