Bennett attended Abbotsfield School and started his football career as an apprentice with West Ham United in 1961.

[2][3] He joined the club along with John Sissons after the pair were spotted by scout Charlie Faulkner while playing for Middlesex Schoolboys.

[4] He played in the side that won the FA Youth Cup in 1963, wearing the number 8 shirt in a team that featured the likes of Harry Redknapp and John Charles.

He signed professional forms later that year and made his First Division debut on 4 April 1964, a home game against Bolton Wanderers.

His career was ended by an ankle injury, and he retired after the 1978–79 season, having made in excess of 200 appearances in all competitions for the O's during his seven years at the club.