| 3. Journée | 07.09.1929 | West Ham United | - | Middlesbrough FC | 5:3 |  |
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| 4. Journée | 09.09.1929 | Sheffield United | - | Middlesbrough FC | 1:3 | |
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| 5. Journée | 14.09.1929 | Middlesbrough FC | - | Manchester United | 2:3 | ||||
| 7. Journée | 18.09.1929 | Bolton Wanderers | - | Middlesbrough FC | 2:2 | |
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| 6. Journée | 21.09.1929 | Grimsby Town | - | Middlesbrough FC | 0:3 | ||||
| 8. Journée | 28.09.1929 | Middlesbrough FC | - | Leicester City | 0:2 | ||||
| 10. Journée | 12.10.1929 | Middlesbrough FC | - | Huddersfield Town | 1:3 | ||||
| 11. Journée | 19.10.1929 | Everton FC | - | Middlesbrough FC | 3:2 | |
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| 12. Journée | 26.10.1929 | Middlesbrough FC | - | Derby County | 4:0 | ||||
| 13. Journée | 02.11.1929 | Manchester City | - | Middlesbrough FC | 3:1 | ||||
| 14. Journée | 09.11.1929 | Middlesbrough FC | - | Sunderland AFC | 3:0 |
Écosse