| Chelsea FC v Aston Villa FC 24/01/1959 | £3.50 | |
| Chelsea FC v Aston Villa FC 24/01/1959 | £7.50 | |
| Aston Villa FC v Chelsea FC 31/01/1959 | View match | |
| Chelsea FC v West Ham United FC 07/02/1959 | £12.99 | |
| Chelsea FC v Burnley FC 21/02/1959 | View match | |
| Bolton Wanderers FC v Chelsea FC 04/03/1959 | View match | |
| Chelsea FC v Luton Town FC 07/03/1959 | View match | |
| Leicester City FC v Chelsea FC 14/03/1959 | View match | |
| Chelsea FC v Preston North End FC 21/03/1959 | View match | |
| Blackpool FC v Chelsea FC 27/03/1959 | View match | |
| Leeds United FC v Chelsea FC 28/03/1959 | View match | |
| Chelsea FC v Blackpool FC 30/03/1959 | View match |