| Middlesbrough FC v Leeds United FC 26/08/2000 | View match | |
| Derby County FC v Middlesbrough FC 06/09/2000 | View match | |
| Middlesbrough FC v Everton FC 09/09/2000 | View match | |
| Manchester City FC v Middlesbrough FC 17/09/2000 | £2.00 | |
| Middlesbrough FC v Macclesfield Town FC 19/09/2000 | View match | |
| Middlesbrough FC v Aston Villa FC 23/09/2000 | View match | |
| Macclesfield Town FC v Middlesbrough FC 26/09/2000 | View match | |
| Southampton FC v Middlesbrough FC 30/09/2000 | £2.50 | |
| Southampton FC v Middlesbrough FC 30/09/2000 | £2.50 | |
| Middlesbrough FC v Newcastle United FC 16/10/2000 | View match | |
| Charlton Athletic FC v Middlesbrough FC 21/10/2000 | £5.50 | |
| Ipswich Town FC v Middlesbrough FC 28/10/2000 | £4.50 |