2. Round | 20/08/2021 | Middlesbrough FC U23 | - | Aston Villa U23 | 1:2 | ||||
3. Round | 29/08/2021 | Middlesbrough FC U23 | - | Southampton FC U23 | 2:1 | ||||
4. Round | 13/09/2021 | Middlesbrough FC U23 | - | Stoke City U23 | 2:0 | ||||
5. Round | 20/09/2021 | Sunderland AFC U23 | - | Middlesbrough FC U23 | 1:3 | ||||
6. Round | 24/09/2021 | Middlesbrough FC U23 | - | Nottingham Forest U23 | 0:1 | ||||
7. Round | 01/10/2021 | Newcastle United U23 | - | Middlesbrough FC U23 | 4:1 | ||||
8. Round | 17/10/2021 | Middlesbrough FC U23 | - | West Bromwich Albion U23 | 1:2 | ||||
9. Round | 22/10/2021 | Burnley FC U23 | - | Middlesbrough FC U23 | 2:0 | ||||
26. Round | 01/05/2022 | Middlesbrough FC U23 | - | Reading FC U23 | 2:1 |