| Chelsea FC v Newcastle United FC 09/04/2000 | £10.00 | |
| Chelsea FC v Coventry City FC 12/04/2000 | £4.00 | |
| Sheffield Wednesday FC v Chelsea FC 15/04/2000 | £3.00 | |
| Barcelona v Chelsea FC 18/04/2000 | £13.99 | |
| Chelsea FC v Middlesbrough FC 22/04/2000 | £3.00 | |
| Chelsea FC v Liverpool FC 29/04/2000 | £3.50 | |
| Arsenal FC v Chelsea FC 06/05/2000 | £1.50 | |
| Arsenal FC v Chelsea FC 06/05/2000 | £3.50 | |
| Chelsea FC v Derby County FC 14/05/2000 | £3.00 | |
| Aston Villa FC v Chelsea FC 20/05/2000 | £9.50 | |
| Aston Villa FC v Chelsea FC 20/05/2000 | £7.50 | |
| Chelsea FC v Manchester United FC 13/08/2000 | £5.50 |