1. Round | 19/08/1950 | Portsmouth FC | - | Middlesbrough FC | 1:1 | ||||
2. Round | 23/08/1950 | Middlesbrough FC | - | Everton FC | 4:0 | ||||
3. Round | 26/08/1950 | Middlesbrough FC | - | Chelsea FC | 3:0 | ||||
4. Round | 30/08/1950 | Everton FC | - | Middlesbrough FC | 3:2 | ||||
5. Round | 02/09/1950 | Burnley FC | - | Middlesbrough FC | 3:1 | ||||
11. Round | 30/09/1950 | Middlesbrough FC | - | Huddersfield Town | 8:0 | ||||
12. Round | 07/10/1950 | Wolverhampton Wanderers | - | Middlesbrough FC | 3:4 | ||||
13. Round | 14/10/1950 | Middlesbrough FC | - | Sunderland AFC | 1:1 | ||||
14. Round | 21/10/1950 | Liverpool FC | - | Middlesbrough FC | 0:0 | ||||
15. Round | 28/10/1950 | Middlesbrough FC | - | Fulham FC | 1:1 | ||||
16. Round | 04/11/1950 | Aston Villa | - | Middlesbrough FC | 0:1 |