| Chelsea FC v West Ham United FC 19/09/1959 | £7.50 | |
| Fulham FC v Chelsea FC 26/09/1959 | £2.92 | |
| Luton Town FC v Chelsea FC 17/10/1959 | £8.50 | |
| Manchester City FC v Chelsea FC 14/11/1959 | £5.00 | |
| Chelsea FC v Arsenal FC 21/11/1959 | £9.99 | |
| Chelsea FC v Sheffield Wednesday FC 05/12/1959 | £4.50 | |
| West Ham United FC v Chelsea FC 06/02/1960 | £5.00 | |
| Chelsea FC v Fulham FC 13/02/1960 | £5.50 | |
| Chelsea FC v Fulham FC 13/02/1960 | £5.00 | |
| Chelsea FC v Fulham FC 13/02/1960 | £6.50 | |
| Blackburn Rovers FC v Chelsea FC 30/03/1960 | £8.50 | |
| Chelsea FC v Manchester City FC 02/04/1960 | £5.50 |