| 1. Round | 30/08/1919 | The Wednesday FC | - | Middlesbrough FC | 0:1 |  |
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| 2. Round | 03/09/1919 | Middlesbrough FC | - | Blackburn Rovers | 2:2 | ||||
| 3. Round | 06/09/1919 | Middlesbrough FC | - | The Wednesday FC | 3:0 | ||||
| 5. Round | 13/09/1919 | Middlesbrough FC | - | Sheffield United | 1:0 | ||||
| 4. Round | 15/09/1919 | Blackburn Rovers | - | Middlesbrough FC | 0:2 | ||||
| 41. Round | 17/09/1919 | Middlesbrough FC | - | Bolton Wanderers | 1:3 | ||||
| 6. Round | 20/09/1919 | Sheffield United | - | Middlesbrough FC | 5:1 | ||||
| 7. Round | 27/09/1919 | Middlesbrough FC | - | Manchester United | 1:1 | ||||
| 8. Round | 04/10/1919 | Manchester United | - | Middlesbrough FC | 1:1 | ||||
| 9. Round | 11/10/1919 | Middlesbrough FC | - | Oldham Athletic | 1:0 | ||||
| 10. Round | 18/10/1919 | Oldham Athletic | - | Middlesbrough FC | 1:2 | ||||
| 11. Round | 25/10/1919 | Middlesbrough FC | - | Aston Villa | 1:4 | ||||
| 16. Round | 29/11/1919 | Chelsea FC | - | Middlesbrough FC | 3:1 | |
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| 14. Round | 03/12/1919 | Newcastle United | - | Middlesbrough FC | 0:0 |
England