| 2. Ronde | 31.08.1927 | Middlesbrough FC | - | Tottenham Hotspur | 3:1 |  |
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| 3. Ronde | 03.09.1927 | Middlesbrough FC | - | Everton FC | 4:2 | ||||
| 5. Ronde | 10.09.1927 | Cardiff City | - | Middlesbrough FC | 1:1 | ||||
| 4. Ronde | 12.09.1927 | Tottenham Hotspur | - | Middlesbrough FC | 4:2 | ||||
| 7. Ronde | 24.09.1927 | Bolton Wanderers | - | Middlesbrough FC | 0:0 | ||||
| 8. Ronde | 01.10.1927 | Middlesbrough FC | - | The Wednesday FC | 3:3 | |
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| 26. Ronde | 23.02.1928 | Blackburn Rovers | - | Middlesbrough FC | 3:0 | ||||
| 33. Ronde | 17.03.1928 | Sheffield United | - | Middlesbrough FC | 4:1 | ||||
| 29. Ronde | 21.03.1928 | Middlesbrough FC | - | Aston Villa | 0:0 |
Schotland