| 1. Round | 20/08/1949 | Middlesbrough FC | - | Everton FC | 0:1 | ||||
| 7. Round | 10/09/1949 | Wolverhampton Wanderers | - | Middlesbrough FC | 3:1 | ||||
| 9. Round | 17/09/1949 | Middlesbrough FC | - | Aston Villa | 0:2 | ||||
| 36. Round | 01/04/1950 | West Bromwich Albion | - | Middlesbrough FC | 0:3 | ||||
| 37. Round | 07/04/1950 | Sunderland AFC | - | Middlesbrough FC | 2:0 | ||||
| 38. Round | 08/04/1950 | Middlesbrough FC | - | Bolton Wanderers | 2:0 | ||||
| 39. Round | 10/04/1950 | Middlesbrough FC | - | Sunderland AFC | 2:0 | ||||
| 40. Round | 15/04/1950 | Birmingham City | - | Middlesbrough FC | 0:0 | ||||
| 41. Round | 22/04/1950 | Middlesbrough FC | - | Stoke City | 2:0 | ||||
| 42. Round | 29/04/1950 | Burnley FC | - | Middlesbrough FC | 3:2 | ||||
| 8. Round | 06/05/1950 | Fulham FC | - | Middlesbrough FC | 1:2 |
Ireland