| Sunderland FC v Coventry City FC 29/08/1999 | View match | |
| Sunderland FC v Leicester City FC 11/09/1999 | View match | |
| Sunderland FC v Walsall FC 14/09/1999 | View match | |
| Derby County FC v Sunderland FC 18/09/1999 | View match | |
| Walsall FC v Sunderland FC 21/09/1999 | View match | |
| Sunderland FC v Sheffield Wednesday FC 25/09/1999 | View match | |
| Bradford City FC v Sunderland FC 02/10/1999 | View match | |
| Wimbledon v Sunderland FC 12/10/1999 | View match | |
| Sunderland FC v Aston Villa FC 18/10/1999 | View match | |
| West Ham United FC v Sunderland FC 24/10/1999 | View match | |
| Sunderland FC v Tottenham Hotspur FC 31/10/1999 | £6.50 | |
| Middlesbrough FC v Sunderland FC 06/11/1999 | View match |