| Chelsea FC v Sunderland FC 07/08/1999 | £3.00 | |
| Chelsea FC v Sunderland FC 07/08/1999 | £4.00 | |
| Chelsea FC v Sunderland FC 07/08/1999 | £1.30 | |
| Chelsea FC v Sunderland FC 07/08/1999 | £3.50 | |
| West Ham United FC v Sunderland FC 24/10/1999 | £5.00 | |
| Sunderland FC v Tottenham Hotspur FC 31/10/1999 | £6.50 | |
| Sunderland FC v Chelsea FC 04/12/1999 | £3.50 | |
| Sunderland FC v Southampton FC 18/12/1999 | £4.00 | |
| Southampton FC v Sunderland FC 01/04/2000 | £3.50 | |
| Sheffield Wednesday FC v Sunderland FC 22/04/2000 | £4.00 | |
| Sunderland FC v West Ham United FC 06/05/2000 | £5.00 | |
| Tottenham Hotspur FC v Sunderland FC 14/05/2000 | £5.00 |