| 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 | |
| West Ham United FC v Middlesbrough FC 16/05/1999 | £5.00 | |
| Aston Villa FC v Middlesbrough FC 28/08/1999 | £2.50 | |
| Middlesbrough FC v Southampton FC 11/09/1999 | £6.50 | |
| Middlesbrough FC v West Ham United FC 17/10/1999 | £5.00 | |
| Arsenal FC v Middlesbrough FC 20/11/1999 | £4.00 | |
| Arsenal FC v Middlesbrough FC 20/11/1999 | £2.50 | |
| Wrexham FC v Middlesbrough FC 11/12/1999 | £6.99 |