| Chelsea FC v Hertha BSC Berlin 03/11/1999 | £5.00 | |
| Chelsea FC v West Ham United FC 07/11/1999 | £3.50 | |
| Chelsea FC v West Ham United FC 07/11/1999 | £3.00 | |
| Everton FC v Chelsea FC 20/11/1999 | £3.50 | |
| Chelsea FC v Feyenoord 24/11/1999 | £3.00 | |
| Chelsea FC v Feyenoord 24/11/1999 | £4.00 | |
| Chelsea FC v Bradford City FC 28/11/1999 | View match | |
| Sunderland FC v Chelsea FC 04/12/1999 | £3.50 | |
| 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 |