| Bradford City FC v Chelsea FC 22/08/2000 | £1.80 | |
| Aston Villa FC v Chelsea FC 27/08/2000 | £4.00 | |
| Chelsea FC v Arsenal FC 06/09/2000 | View match | |
| Newcastle United FC v Chelsea FC 09/09/2000 | £3.50 | |
| Chelsea FC v St Gallen 14/09/2000 | £5.50 | |
| Chelsea FC v Leicester City FC 17/09/2000 | £3.50 | |
| Chelsea FC v Leicester City FC 17/09/2000 | £3.00 | |
| Manchester United FC v Chelsea FC 23/09/2000 | View match | |
| St Gallen v Chelsea FC 28/09/2000 | View match | |
| Chelsea FC v Liverpool FC 01/10/2000 | £4.50 | |
| Sunderland FC v Chelsea FC 14/10/2000 | £4.50 | |
| Chelsea FC v Coventry City FC 21/10/2000 | £3.50 |