| Lazio SS v Chelsea FC 07/12/1999 | £10.00 | |
| Hull City FC v Chelsea FC 11/12/1999 | View match | |
| Chelsea FC v Leeds United FC 19/12/1999 | £3.00 | |
| Southampton FC v Chelsea FC 26/12/1999 | £3.50 | |
| Southampton FC v Chelsea FC 26/12/1999 | £2.50 | |
| Southampton FC v Chelsea FC 26/12/1999 | £3.00 | |
| Southampton FC v Chelsea FC 26/12/1999 | £3.00 | |
| Chelsea FC v Sheffield Wednesday FC 29/12/1999 | £3.00 | |
| Coventry City FC v Chelsea FC 04/01/2000 | £3.50 | |
| 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 |