| 11. Round | 19/10/1929 | Everton FC | - | Middlesbrough FC | 3:2 | ||||
| 12. Round | 26/10/1929 | Middlesbrough FC | - | Derby County | 4:0 | ||||
| 13. Round | 02/11/1929 | Manchester City | - | Middlesbrough FC | 3:1 | ||||
| 14. Round | 09/11/1929 | Middlesbrough FC | - | Sunderland AFC | 3:0 | ||||
| 24. Round | 04/01/1930 | Middlesbrough FC | - | West Ham United | 2:0 | ||||
| 29. Round | 26/03/1930 | Huddersfield Town | - | Middlesbrough FC | 1:0 | ||||
| 35. Round | 29/03/1930 | Aston Villa | - | Middlesbrough FC | 4:2 | ||||
| 36. Round | 05/04/1930 | Middlesbrough FC | - | Leeds United | 1:1 |
England