| Sunderland FC v Birmingham City FC 09/05/1999 | View match | |
| Sunderland FC v All Stars XI 11/05/1999 | View match | |
| Rangers (Glasgow) FC v Sunderland FC 21/07/1999 | View match | |
| Preston North End FC v Sunderland FC 29/07/1999 | View match | |
| Sunderland FC v Sampdoria 31/07/1999 | View match | |
| 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 | £3.00 | |
| Chelsea FC v Sunderland FC 07/08/1999 | £3.50 | |
| Sunderland FC v Watford FC 10/08/1999 | View match | |
| Sunderland FC v Arsenal FC 14/08/1999 | View match | |
| Leeds United FC v Sunderland FC 21/08/1999 | View match |