From Wangaratta, Victoria, Hickmott originally played for Tarrawingee in the Ovens & King Football League and the Wangaratta Rovers in the Ovens & Murray Football League (O&M).
He was recruited by the Essendon Football Club after starring in the Wangaratta Rovers 1988 O&M grand final win.
He spent 1989 playing in Essendon's reserve side and entered the 1990 AFL Pre-season Draft where he was selected by Melbourne with the 45th pick overall.
In 2001, racehorse owner Lloyd Williams offered him a position at his stables, which he accepted.
[6] Green Moon, the winner of the 2012 Melbourne Cup, was trained by Hickmott,[7] and also won the Turnbull Stakes in 2012.