| 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 | £4.50 | |
| Chelsea FC v West Bromwich Albion FC 31/12/1988 | £4.00 | |
| 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 | £4.50 | |
| Chelsea FC v Nottingham Forest FC 10/01/1989 | £3.50 | |
| Chelsea FC v Crystal Palace FC 14/01/1989 | £4.50 | |
| Blackburn Rovers FC v Chelsea FC 21/01/1989 | View match | |
| Swansea City FC v Chelsea FC 27/01/1989 | View match | |
| Walsall FC v Chelsea FC 04/02/1989 | £4.50 |