| Bradford City FC v Chelsea FC 19/11/1988 | £4.50 | |
| Chelsea FC v Shrewsbury Town FC 26/11/1988 | £4.50 | |
| Stoke City FC v Chelsea FC 03/12/1988 | £4.50 | |
| Chelsea FC v Portsmouth FC 10/12/1988 | £4.00 | |
| Chelsea FC v Portsmouth FC 10/12/1988 | £4.50 | |
| Birmingham City FC v Chelsea FC 16/12/1988 | £4.50 | |
| Chelsea FC v Ipswich Town FC 26/12/1988 | £4.50 | |
| Chelsea FC v West Bromwich Albion FC 31/12/1988 | £4.00 | |
| Chelsea FC v West Bromwich Albion FC 31/12/1988 | £4.50 | |
| Oxford United FC v Chelsea FC 02/01/1989 | £4.50 | |
| Barnsley FC v Chelsea FC 07/01/1989 | £4.50 | |
| Chelsea FC v Nottingham Forest FC 10/01/1989 | £3.50 |