Simpson began his playing career with hometown club Chesterfield, where he progressed through the youth ranks to make more than 40 league appearances.
[1] This came after Chester had been unsuccessful in attempting to sign Simpson's Chesterfield colleague Ernie Moss to strengthen their squad of just 14 professional players.
[1] Simpson marked his competitive debut with a goal in a Football League Trophy tie against Bury.
[2] His tally included two goals on his return to Chesterfield, as Chester registered a shock 5–3 win in monsoon conditions.
[3] He joined Oswestry Town[4] but then played for Bangor City in the Alliance Premier League later in the 1983–84 season.