| Middlesbrough FC v Blackburn Rovers FC 08/12/2018 | £6.50 | |
| Reading FC v Middlesbrough FC 22/12/2018 | £7.50 | |
| Middlesbrough FC v Peterborough United FC 05/01/2019 | £6.50 | |
| Middlesbrough FC v Millwall FC 19/01/2019 | £6.50 | |
| Newport County AFC v Middlesbrough FC 05/02/2019 | £6.50 | |
| Luton Town FC v Middlesbrough FC 02/08/2019 | £6.75 | |
| Middlesbrough FC v Millwall FC 24/08/2019 | £9.99 | |
| Cardiff City FC v Middlesbrough FC 21/09/2019 | £7.50 | |
| Huddersfield Town FC v Middlesbrough FC 23/10/2019 | £6.75 | |
| Middlesbrough FC v Tottenham Hotspur FC 05/01/2020 | £9.50 | |
| Middlesbrough FC v Tottenham Hotspur FC 05/01/2020 | £8.50 | |
| Tottenham Hotspur FC v Middlesbrough FC 14/01/2020 | £7.00 |