Stewart started his football career as a junior playing for Linfield, Crusaders and Windsor Youth before joining Glentoran.
[5][6] However, on 21 August 2015 and several days after an unofficial announcement, Glentoran confirmed Stewart would move to Swindon Town[7] in an undisclosed deal was believed to be between £50,000 and £55,000.
Glentoran therefore refused to sign the deal and referred the matter to the Irish Football Association who confirmed that they would have blocked the players registration.
[12] Preceding his release from Swindon, on 8 May 2017 and despite promising to re-join Glentoran, Stewart returned to Northern Ireland accepting a much higher wage to join Linfield.
[13] On 28 June 2017, Stewart scored on his Linfield debut in their UEFA Champions League qualifier against La Fiorita, netting the winner in their 1–0 victory in the 89th minute.
Stewart has represented Northern Ireland national football team at Under-19 level, making his debut in the 1–1 draw against France.