| Tottenham Hotspur FC v Middlesbrough FC 13/09/1998 | £4.00 | |
| Middlesbrough FC v Wycombe Wanderers FC 16/09/1998 | View match | |
| Middlesbrough FC v Everton FC 19/09/1998 | View match | |
| Wycombe Wanderers FC v Middlesbrough FC 22/09/1998 | View match | |
| Chelsea FC v Middlesbrough FC 26/09/1998 | £1.00 | |
| Middlesbrough FC v Sheffield Wednesday FC 03/10/1998 | View match | |
| Shelbourne (Ireland) v Middlesbrough FC 06/10/1998 | View match | |
| Middlesbrough FC v Blackburn Rovers FC 17/10/1998 | View match | |
| Wimbledon v Middlesbrough FC 24/10/1998 | View match | |
| Middlesbrough FC v Everton FC 28/10/1998 | View match | |
| Middlesbrough FC v Nottingham Forest FC 01/11/1998 | View match | |
| Southampton FC v Middlesbrough FC 07/11/1998 | View match |