| Chelsea FC v Middlesbrough FC 22/04/2000 | £3.00 | |
| Manchester United FC v Chelsea FC 24/04/2000 | View match | |
| Chelsea FC v Liverpool FC 29/04/2000 | £3.50 | |
| Arsenal FC v Chelsea FC 06/05/2000 | £3.50 | |
| Arsenal FC v Chelsea FC 06/05/2000 | £1.50 | |
| Chelsea FC v Derby County FC 14/05/2000 | £3.00 | |
| Aston Villa FC v Chelsea FC 20/05/2000 | £7.50 | |
| Aston Villa FC v Chelsea FC 20/05/2000 | £9.50 | |
| Chelsea FC v Manchester United FC 13/08/2000 | £5.50 | |
| Chelsea FC v Manchester United FC 13/08/2000 | View match | |
| Chelsea FC v Manchester United FC 13/08/2000 | £6.50 | |
| Chelsea FC v West Ham United FC 19/08/2000 | £4.50 |