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| Preston North End FC v Middlesbrough FC 27/11/2018 | View match | |
| Middlesbrough FC v Aston Villa FC 01/12/2018 | View match | |
| Middlesbrough FC v Blackburn Rovers FC 08/12/2018 | £6.50 | |
| Queens Park Rangers FC v Middlesbrough FC 15/12/2018 | View match | |
| Middlesbrough FC v Burton Albion FC 18/12/2018 | View match | |
| Reading FC v Middlesbrough FC 22/12/2018 | £7.50 | |
| Middlesbrough FC v Sheffield Wednesday FC 26/12/2018 | View match | |
| Middlesbrough FC v Ipswich Town FC 29/12/2018 | View match | |
| Derby County FC v Middlesbrough FC 01/01/2019 | View match | |
| Middlesbrough FC v Peterborough United FC 05/01/2019 | £6.50 | |
| Birmingham City FC v Middlesbrough FC 12/01/2019 | View match |