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| Luton Town FC v Middlesbrough FC 02/08/2019 | £6.75 | |
| Middlesbrough FC v Brentford FC 10/08/2019 | View match | |
| Middlesbrough FC v Crewe Alexandra FC 13/08/2019 | View match | |
| Blackburn Rovers FC v Middlesbrough FC 17/08/2019 | View match | |
| Middlesbrough FC v Wigan Athletic FC 20/08/2019 | View match | |
| Middlesbrough FC v Millwall FC 24/08/2019 | £9.99 | |
| Bristol City FC v Middlesbrough FC 31/08/2019 | View match | |
| Middlesbrough FC v Reading FC 14/09/2019 | View match | |
| Cardiff City FC v Middlesbrough FC 21/09/2019 | £7.50 | |
| Middlesbrough FC v Sheffield Wednesday FC 28/09/2019 | View match |