| Middlesbrough FC v Oldham Athletic FC 16/11/1985 | View match | |
| Millwall FC v Middlesbrough FC 23/11/1985 | View match | |
| Middlesbrough FC v Shrewsbury Town FC 30/11/1985 | View match | |
| Stoke City FC v Middlesbrough FC 07/12/1985 | View match | |
| Middlesbrough FC v Wimbledon 14/12/1985 | View match | |
| Fulham FC v Middlesbrough FC 21/12/1985 | £4.00 | |
| Carlisle United FC v Middlesbrough FC 26/12/1985 | View match | |
| Middlesbrough FC v Sunderland FC 28/12/1985 | View match | |
| Middlesbrough FC v Huddersfield Town FC 01/01/1986 | View match | |
| Norwich City FC v Middlesbrough FC 11/01/1986 | View match | |
| Middlesbrough FC v Southampton FC 13/01/1986 | View match | |
| Brighton & Hove Albion FC v Middlesbrough FC 18/01/1986 | £4.50 |