| 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 | |
| Arsenal FC v Middlesbrough FC 20/11/1999 | £3.50 | |
| 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 | |
| Southampton FC v Middlesbrough FC 04/03/2000 | £3.50 | |
| Tottenham Hotspur FC v Middlesbrough FC 03/04/2000 | £3.00 |