| Middlesbrough FC v Sunderland FC 06/11/1999 | View match | |
| Arsenal FC v Middlesbrough FC 20/11/1999 | £4.00 | |
| Middlesbrough FC v Wimbledon 27/11/1999 | View match | |
| Middlesbrough FC v Arsenal FC 30/11/1999 | View match | |
| Bradford City FC v Middlesbrough FC 04/12/1999 | View match | |
| Wrexham FC v Middlesbrough FC 11/12/1999 | View match | |
| Tranmere Rovers FC v Middlesbrough FC 14/12/1999 | View match | |
| Middlesbrough FC v Tottenham Hotspur FC 18/12/1999 | £4.50 | |
| Sheffield Wednesday FC v Middlesbrough FC 26/12/1999 | £4.00 | |
| Middlesbrough FC v Derby County FC 15/01/2000 | View match | |
| Liverpool FC v Middlesbrough FC 22/01/2000 | £3.50 | |
| Manchester United FC v Middlesbrough FC 29/01/2000 | View match |