| 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 | £2.50 | |
| Arsenal FC v Middlesbrough FC 20/11/1999 | £4.00 | |
| Wrexham FC v Middlesbrough FC 11/12/1999 | £6.99 | |
| Middlesbrough FC v Tottenham Hotspur FC 18/12/1999 | £4.50 | |
| Sheffield Wednesday FC v Middlesbrough FC 26/12/1999 | £4.00 | |
| Liverpool FC v Middlesbrough FC 22/01/2000 | £3.50 |