| Middlesbrough FC v Wimbledon 05/04/1999 | View match | |
| Middlesbrough FC v Charlton Athletic FC 10/04/1999 | £4.00 | |
| Middlesbrough FC v Chelsea FC 14/04/1999 | £3.50 | |
| 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 |