| Wimbledon v Middlesbrough FC 17/08/1985 | View match | |
| Mansfield Town FC v Middlesbrough FC 21/08/1985 | View match | |
| Middlesbrough FC v Fulham FC 24/08/1985 | View match | |
| Charlton Athletic FC v Middlesbrough FC 27/08/1985 | £3.00 | |
| Middlesbrough FC v Brighton & Hove Albion FC 31/08/1985 | £5.00 | |
| Middlesbrough FC v Mansfield Town FC 03/09/1985 | View match | |
| Hull City FC v Middlesbrough FC 07/09/1985 | View match | |
| Middlesbrough FC v Stoke City FC 10/09/1985 | View match | |
| Middlesbrough FC v Norwich City FC 14/09/1985 | View match | |
| Sheffield United FC v Middlesbrough FC 21/09/1985 | View match | |
| Middlesbrough FC v Barnsley FC 28/09/1985 | View match | |
| Middlesbrough FC v Crystal Palace FC 05/10/1985 | View match |