Bennett grew up in Perth, Western Australia where he began playing Australian rules football, first playing senior football with East Fremantle in the West Australian Football League. His career with the Sharks was severely affected by injuries to his knee, which kept him out for over a season during 1985 and 1986 – in the interim denying him a WAFL premiership. However, training with former star Harry Neesham allowed Bennett to be fit for the 1986 finals, and in the second semi he became the first player ever to score ten goals in a WA(N)FL final.