| 1. Round | 30/08/1919 | Derby County | - | Manchester United | 1:1 | ||||
| 2. Round | 01/09/1919 | Manchester United | - | The Wednesday FC | 0:0 | ||||
| 3. Round | 06/09/1919 | Manchester United | - | Derby County | 0:2 | ||||
| 4. Round | 08/09/1919 | The Wednesday FC | - | Manchester United | 1:3 | ||||
| 5. Round | 13/09/1919 | Preston North End | - | Manchester United | 2:3 | ||||
| 6. Round | 20/09/1919 | Manchester United | - | Preston North End | 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 | Manchester City | - | Manchester United | 3:3 |  |
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| 10. Round | 18/10/1919 | Manchester United | - | Manchester City | 1:0 | ||||
| 11. Round | 25/10/1919 | Sheffield United | - | Manchester United | 2:2 | ||||
| 13. Round | 08/11/1919 | Burnley FC | - | Manchester United | 2:1 | |
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| 15. Round | 22/11/1919 | Oldham Athletic | - | Manchester United | 0:3 | ||||
| 17. Round | 06/12/1919 | Aston Villa | - | Manchester United | 2:0 | ||||
| 18. Round | 13/12/1919 | Manchester United | - | Aston Villa | 1:2 | ||||
| 19. Round | 20/12/1919 | Manchester United | - | Newcastle United | 2:1 |
Scotland