| Middlesbrough FC v Leicester City FC 30/01/1999 | View match | |
| Liverpool FC v Middlesbrough FC 06/02/1999 | £5.00 | |
| Everton FC v Middlesbrough FC 17/02/1999 | View match | |
| Middlesbrough FC v Tottenham Hotspur FC 20/02/1999 | £5.00 | |
| Sheffield Wednesday FC v Middlesbrough FC 27/02/1999 | View match | |
| Rangers (Glasgow) FC v Middlesbrough FC 02/03/1999 | View match | |
| Middlesbrough FC v Southampton FC 14/03/1999 | View match | |
| Nottingham Forest FC v Middlesbrough FC 20/03/1999 | View match | |
| Blackburn Rovers FC v Middlesbrough FC 03/04/1999 | View match | |
| 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 |