| Southampton FC v Chelsea FC 26/12/1999 | £3.50 | |
| Chelsea FC v Sheffield Wednesday FC 29/12/1999 | £3.00 | |
| Coventry City FC v Chelsea FC 04/01/2000 | £3.50 | |
| 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 | |
| Chelsea FC v Leicester City FC 30/01/2000 | £4.50 | |
| Tottenham Hotspur FC v Chelsea FC 05/02/2000 | £4.00 | |
| Tottenham Hotspur FC v Chelsea FC 05/02/2000 | £3.50 | |
| 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 |