Herne Bay Pathway: Featured for the Herne Bay U23s and breaking through to make senior appearances for the 1st Team. He has played for Manager Ben Smith at Canterbury City.

Early Years: he gained valuable experience representing clubs such as Canterbury City, Erith & Belvedere, Bridon Ropes and Sheppey United.

Sittingbourne Breakthrough (2024–2026): Formed the core of an impressive two-season stint with the "Brickies."

2024/25: Played a vital role as a wide midfielder/winger during their historic run to the FA Trophy Quarter-Finals and their progress to the Isthmian League play-off final.

2025/26: After returning from a short spell at Welling United, Henry was a regular choice in their attack, netting 9 goals across all competitions.