| 1. Ronde | 08.08.2021 | Fulham FC | - | Middlesbrough FC | 1:1 | ||||
| 2. Ronde | 14.08.2021 | Middlesbrough FC | - | Bristol City | 2:1 | ||||
| 3. Ronde | 18.08.2021 | Middlesbrough FC | - | Queens Park Rangers | 2:3 | ||||
| 5. Ronde | 28.08.2021 | Middlesbrough FC | - | Blackburn Rovers | 1:1 | ||||
| 6. Ronde | 11.09.2021 | Coventry City | - | Middlesbrough FC | 2:0 |  |
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| 7. Ronde | 15.09.2021 | Nottingham Forest | - | Middlesbrough FC | 0:2 | ||||
| 8. Ronde | 18.09.2021 | Middlesbrough FC | - | Blackpool FC | 1:2 | ||||
| 17. Ronde | 06.11.2021 | West Bromwich Albion | - | Middlesbrough FC | 1:1 |
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