| 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 | |
| Wimbledon v Middlesbrough FC 31/10/2000 | View match | |
| Middlesbrough FC v Arsenal FC 04/11/2000 | View match | |
| Manchester United FC v Middlesbrough FC 11/11/2000 | View match | |
| Middlesbrough FC v Leicester City FC 18/11/2000 | View match |