Bennett began his football career playing for Skelmersdale United and his local team Kirkby Town.
However, Bennett was soon on the move as he followed manager Harry McNally to Chester City, where 'Psycho', as he was known, scored 13 league goals in 43 appearances as the club achieved promotion from Division Four.
[3][2] Bennett scored 23 times in 1986–87 but his season was overshadowed by his tackle in an FA Cup tie against Sheffield Wednesday that left opponent Ian Knight with his leg broken in 7 places.
[7] He remained there until the end of the 1991–92 season, scoring the winner at Stoke City in April 1992 that effectively sealed Division Three survival for Chester.
[2] Bennett spent just a year at Preston for the 1996-97 season but is remembered fondly due to scoring the first and third goals in a riotous match against fierce rivals Blackpool.