2. Round | 04/09/1909 | The Wednesday FC | - | Middlesbrough FC | 1:5 | ||||
3. Round | 11/09/1909 | Middlesbrough FC | - | Woolwich Arsenal | 5:2 | ||||
4. Round | 18/09/1909 | Bristol City | - | Middlesbrough FC | 4:1 | ||||
5. Round | 25/09/1909 | Middlesbrough FC | - | Bolton Wanderers | 1:2 | ||||
22. Round | 22/01/1910 | Woolwich Arsenal | - | Middlesbrough FC | 3:0 |