15. Round | 27/11/1929 | Arsenal FC | - | Middlesbrough FC | 1:2 | ||||
17. Round | 30/11/1929 | Leeds United | - | Middlesbrough FC | 1:2 | ||||
18. Round | 07/12/1929 | Middlesbrough FC | - | Sheffield Wednesday | 4:1 | ||||
19. Round | 14/12/1929 | Burnley FC | - | Middlesbrough FC | 4:1 | ||||
20. Round | 21/12/1929 | Middlesbrough FC | - | Portsmouth FC | 2:0 | ||||
21. Round | 25/12/1929 | Newcastle United | - | Middlesbrough FC | 3:2 | ||||
22. Round | 26/12/1929 | Middlesbrough FC | - | Newcastle United | 2:2 | ||||
23. Round | 28/12/1929 | Liverpool FC | - | Middlesbrough FC | 5:2 | ||||
38. Round | 01/01/1930 | Blackburn Rovers | - | Middlesbrough FC | 7:0 | ||||
25. Round | 18/01/1930 | Manchester United | - | Middlesbrough FC | 0:3 |