| Chelsea FC v Manchester United FC 02/09/1959 | View match | |
| Chelsea FC v Manchester United FC 02/09/1959 | £11.99 | |
| Chelsea FC v Burnley FC 05/09/1959 | View match | |
| Birmingham City FC v Chelsea FC 09/09/1959 | View match | |
| Leeds United FC v Chelsea FC 12/09/1959 | View match | |
| Chelsea FC v Birmingham City FC 16/09/1959 | View match | |
| Chelsea FC v West Ham United FC 19/09/1959 | View match | |
| Fulham FC v Chelsea FC 26/09/1959 | £2.92 | |
| Fulham FC v Chelsea FC 26/09/1959 | View match | |
| West Bromwich Albion FC v Chelsea FC 03/10/1959 | View match | |
| Guildford City v Chelsea FC 03/10/1959 | View match | |
| Chelsea FC v Bolton Wanderers FC 10/10/1959 | View match |