| 2. Round | 31/08/1927 | Middlesbrough FC | - | Tottenham Hotspur | 3:1 |  |
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| 3. Round | 03/09/1927 | Middlesbrough FC | - | Everton FC | 4:2 | ||||
| 5. Round | 10/09/1927 | Cardiff City | - | Middlesbrough FC | 1:1 | ||||
| 4. Round | 12/09/1927 | Tottenham Hotspur | - | Middlesbrough FC | 4:2 | ||||
| 7. Round | 24/09/1927 | Bolton Wanderers | - | Middlesbrough FC | 0:0 | ||||
| 8. Round | 01/10/1927 | Middlesbrough FC | - | The Wednesday FC | 3:3 | |
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| 26. Round | 23/02/1928 | Blackburn Rovers | - | Middlesbrough FC | 3:0 | ||||
| 33. Round | 17/03/1928 | Sheffield United | - | Middlesbrough FC | 4:1 | ||||
| 29. Round | 21/03/1928 | Middlesbrough FC | - | Aston Villa | 0:0 |
Scotland