| 1. Ronde | 20.08.1949 | Middlesbrough FC | - | Everton FC | 0:1 | ||||
| 7. Ronde | 10.09.1949 | Wolverhampton Wanderers | - | Middlesbrough FC | 3:1 | ||||
| 9. Ronde | 17.09.1949 | Middlesbrough FC | - | Aston Villa | 0:2 | ||||
| 36. Ronde | 01.04.1950 | West Bromwich Albion | - | Middlesbrough FC | 0:3 | ||||
| 37. Ronde | 07.04.1950 | Sunderland AFC | - | Middlesbrough FC | 2:0 | ||||
| 38. Ronde | 08.04.1950 | Middlesbrough FC | - | Bolton Wanderers | 2:0 | ||||
| 39. Ronde | 10.04.1950 | Middlesbrough FC | - | Sunderland AFC | 2:0 | ||||
| 40. Ronde | 15.04.1950 | Birmingham City | - | Middlesbrough FC | 0:0 | ||||
| 41. Ronde | 22.04.1950 | Middlesbrough FC | - | Stoke City | 2:0 | ||||
| 42. Ronde | 29.04.1950 | Burnley FC | - | Middlesbrough FC | 3:2 | ||||
| 8. Ronde | 06.05.1950 | Fulham FC | - | Middlesbrough FC | 1:2 |
Ierland