| Coventry City FC v Middlesbrough FC 28/12/1996 | View match | |
| Arsenal FC v Middlesbrough FC 01/01/1997 | £3.00 | |
| Middlesbrough FC v Chester City FC 04/01/1997 | View match | |
| Middlesbrough FC v Liverpool FC 08/01/1997 | View match | |
| Middlesbrough FC v Southampton FC 11/01/1997 | View match | |
| Middlesbrough FC v Sheffield Wednesday FC 18/01/1997 | View match | |
| Middlesbrough FC v Hednesford Town F.C 25/01/1997 | View match | |
| Hednesford Town F.C v Middlesbrough FC 25/01/1997 | View match | |
| Wimbledon v Middlesbrough FC 01/02/1997 | View match | |
| Manchester City FC v Middlesbrough FC 15/02/1997 | £6.00 | |
| Middlesbrough FC v Newcastle United FC 22/02/1997 | View match | |
| Stockport County FC v Middlesbrough FC 26/02/1997 | View match |