1. Round | 31/08/1929 | Middlesbrough FC | - | Liverpool FC | 5:0 | ||||
2. Round | 04/09/1929 | Middlesbrough FC | - | Sheffield United | 3:1 | ||||
3. Round | 07/09/1929 | West Ham United | - | Middlesbrough FC | 5:3 | ||||
4. Round | 09/09/1929 | Sheffield United | - | Middlesbrough FC | 1:3 | ||||
5. Round | 14/09/1929 | Middlesbrough FC | - | Manchester United | 2:3 | ||||
26. Round | 05/03/1930 | Middlesbrough FC | - | Grimsby Town | 1:5 |