| Bradford City FC v Chelsea FC 08/01/2000 | View match | |
| Chelsea FC v Tottenham Hotspur FC 12/01/2000 | £4.00 | |
| Chelsea FC v Leicester City FC 15/01/2000 | £3.00 | |
| Chelsea FC v Nottingham Forest FC 19/01/2000 | £3.50 | |
| Aston Villa FC v Chelsea FC 22/01/2000 | View match | |
| Chelsea FC v Leicester City FC 30/01/2000 | £4.50 | |
| Tottenham Hotspur FC v Chelsea FC 05/02/2000 | £3.50 | |
| Tottenham Hotspur FC v Chelsea FC 05/02/2000 | £4.00 | |
| Tottenham Hotspur FC v Chelsea FC 05/02/2000 | £3.00 | |
| Tottenham Hotspur FC v Chelsea FC 05/02/2000 | £4.50 | |
| Chelsea FC v Wimbledon 12/02/2000 | £3.00 | |
| Chelsea FC v Gillingham FC 20/02/2000 | View match |