| Coventry City FC v Middlesbrough FC 17/04/1999 | View match | |
| Middlesbrough FC v Arsenal FC 24/04/1999 | View match | |
| Newcastle United FC v Middlesbrough FC 01/05/1999 | View match | |
| Middlesbrough FC v Manchester United FC 09/05/1999 | View match | |
| West Ham United FC v Middlesbrough FC 16/05/1999 | View match | |
| Middlesbrough FC v Bradford City FC 07/08/1999 | View match | |
| Wimbledon v Middlesbrough FC 10/08/1999 | View match | |
| Derby County FC v Middlesbrough FC 14/08/1999 | View match | |
| Middlesbrough FC v Liverpool FC 21/08/1999 | View match | |
| Middlesbrough FC v Leicester City FC 24/08/1999 | View match | |
| Aston Villa FC v Middlesbrough FC 28/08/1999 | £2.50 | |
| Middlesbrough FC v Southampton FC 11/09/1999 | £6.50 |