[2] Originally drafted to Greater Western Sydney in the 2016 national draft, Cumming plays as a defender and made his debut in round 8, 2018 against the West Coast Eagles at Spotless Stadium.
He played in the North East Australian Football League (NEAFL) for the Western Sydney University Giants (the GWS Giants' NEAFL affiliate).
[5] In the 2023 preliminary final against Collingwood, Cumming scored a goal to set up a 10-point lead at half time, but the Giants went on to lose by a solitary point.
[7] Following the Giants' semi-final exit in 2024, Cumming informed the club of his desire to exercise his free agency, seeking a move to South Australia.
[8] In September 2024, Cumming announced his desire to join the Adelaide during the free agency period, citing fellow Broken Hill native Taylor Walker as a key influence behind the decision.