Stewart started his career with DB Basovak in his hometown of Spanish Town before going on to play football at Innswood High School and Charlie Smith High School, the latter of which he represented in the Manning Cup.[2]
Professional career
He started his professional career with UWI, before a move to Molynes United in 2022.[2] Mid-way through the 2022 season, he moved to Mount Pleasant, where he flourished, scoring five goals in his first four games for the Saint Ann Parish-based club.[3]
On 17 August 2023, Stewart officially joined Italian side Salernitana on a permanent deal, signing a three-year contract with the club, with a further option.[4] In the process, he became the third Jamaican footballer to ever play in Serie A, as well as the first one to join it from his own national league.[5][6]
On 1 October 2023, Trivante made his debut for Salernitana, coming on as a substitute in the 79th minute against Inter Milan. However, Salernitana lost 4–0, with Lautaro Martinez, himself a substitute, scoring all four goals.
On 15 February 2024, Stewart moved to Serbia on loan to Javor Ivanjica with an option to buy.[7]
After completing the season for Javor, Stewart was permanently sold by Salernitana to fellow Serbian club Radnički Niš.[8]