| Chelsea FC v Manchester City FC 04/04/1959 | View match | |
| Arsenal FC v Chelsea FC 11/04/1959 | View match | |
| Nottingham Forest FC v Chelsea FC 15/04/1959 | View match | |
| Chelsea FC v Everton FC 18/04/1959 | View match | |
| Chelsea FC v West Bromwich Albion FC 22/04/1959 | £3.50 | |
| Birmingham City FC v Chelsea FC 25/04/1959 | View match | |
| Chelsea FC v Ville De Belgrade 29/04/1959 | £28.99 | |
| Ville De Belgrade v Chelsea FC 13/05/1959 | View match | |
| Chelsea FC v Preston North End FC 22/08/1959 | £8.00 | |
| Chelsea FC v Preston North End FC 22/08/1959 | £8.50 | |
| Manchester United FC v Chelsea FC 26/08/1959 | View match | |
| Leicester City FC v Chelsea FC 29/08/1959 | View match |