An Academy graduate from Newtown taken by the Sydney Swans with pick 24 in the 2023 national draft, Cleary goaled with his very first kick on debut in Round 15, 2024. He was part of the Allies side that won its maiden under-18 championship in 2023, and collected the club's Lees Family Memorial Trophy the following year. He has played 27 AFL games and kicked 6 goals.