| Luton Town FC v Chelsea FC 17/10/1959 | View match | |
| Ashford Town v Chelsea FC 19/10/1959 | View match | |
| Chelsea FC v Everton FC 24/10/1959 | View match | |
| Nottingham Forest FC v Chelsea FC 31/10/1959 | View match | |
| Chelsea FC v Blackburn Rovers FC 07/11/1959 | View match | |
| Manchester City FC v Chelsea FC 14/11/1959 | £5.00 | |
| Chelsea FC v British Olympic XI 16/11/1959 | View match | |
| Chelsea FC v Arsenal FC 21/11/1959 | View match | |
| Wolverhampton Wanderers FC v Chelsea FC 28/11/1959 | View match | |
| Chelsea FC v Tooting & Mitcham 30/11/1959 | View match | |
| Chelsea FC v Athletico Bilbao 02/12/1959 | View match | |
| Chelsea FC v Sheffield Wednesday FC 05/12/1959 | £4.50 |