| 1. Jornada | 22.08.1959 | Chelsea | - | Preston North End | 4:4 | ||||
| 2. Jornada | 26.08.1959 | Manchester United | - | Chelsea | 0:1 | ||||
| 3. Jornada | 29.08.1959 | Leicester City | - | Chelsea | 3:1 | ||||
| 4. Jornada | 02.09.1959 | Chelsea | - | Manchester United | 3:6 | ||||
| 8. Jornada | 16.09.1959 | Chelsea | - | Birmingham City | 4:2 | ||||
| 9. Jornada | 19.09.1959 | Chelsea | - | West Ham United | 2:4 | ||||
| 25. Jornada | 02.01.1960 | Chelsea | - | Leicester City | 2:2 | ||||
| 33. Jornada | 12.03.1960 | Everton | - | Chelsea | 6:1 |
Irlanda