| Aston Villa FC v Chelsea FC 14/09/1963 | View match | |
| Blackburn Rovers FC v Chelsea FC 16/09/1963 | View match | |
| Chelsea FC v Tottenham Hotspur FC 21/09/1963 | View match | |
| Swindon Town FC v Chelsea FC 25/09/1963 | View match | |
| Chelsea FC v Wolverhampton Wanderers FC 28/09/1963 | View match | |
| Wolverhampton Wanderers FC v Chelsea FC 28/09/1963 | View match | |
| Chelsea FC v Manchester United FC 02/10/1963 | View match | |
| Chelsea FC v Stoke City FC 05/10/1963 | View match | |
| Ipswich Town FC v Chelsea FC 12/10/1963 | View match | |
| Chelsea FC v Sheffield Wednesday FC 19/10/1963 | £2.50 | |
| Dartford v Chelsea FC 22/10/1963 | View match | |
| Fulham FC v Chelsea FC 26/10/1963 | £3.50 |