| Arsenal FC v Middlesbrough FC 29/11/1998 | £3.00 | |
| Manchester United FC v Middlesbrough FC 19/12/1998 | £4.50 | |
| Manchester United FC v Middlesbrough FC 19/12/1998 | £6.00 | |
| Manchester United FC v Middlesbrough FC 03/01/1999 | £7.00 | |
| Liverpool FC v Middlesbrough FC 06/02/1999 | £5.00 | |
| Middlesbrough FC v Tottenham Hotspur FC 20/02/1999 | £5.00 | |
| Middlesbrough FC v Charlton Athletic FC 10/04/1999 | £4.00 | |
| Middlesbrough FC v Chelsea FC 14/04/1999 | £3.50 | |
| Aston Villa FC v Middlesbrough FC 28/08/1999 | £2.50 | |
| Arsenal FC v Middlesbrough FC 20/11/1999 | £4.00 | |
| Middlesbrough FC v Tottenham Hotspur FC 18/12/1999 | £4.50 | |
| Sheffield Wednesday FC v Middlesbrough FC 26/12/1999 | £4.00 |