Chalmers played for Corby Town before signing for Leicester City in 1956. Nicknamed 'Chopper' for his fully committed playing style, Chalmers played 80 minutes of the 1961 FA Cup Final hobbling on the wing after suffering a badly gashed shin which rendered him no more than nuisance value as no substitutions were then allowed. Leicester City lost 2–0 to Tottenham Hotspur. After leaving Notts County, he played non-league football for Dunstable Town.