Plan de juego
| Fecha | Ronda | Partido | Partido | Res. | Espectadores | |
|---|---|---|---|---|---|---|
| 14.01.2023 |  | 15. Jornada | Middlesbrough FC - Nottingham Forest | - NOT | 0:4 | |
| 27.01.2023 |  | 14. Jornada | Middlesb. U21 - Southampt. U21 | - | 2:2 | 50 |
| 28.01.2023 | | 17. Jornada | Middlesbrough FC - Liverpool FC | - | 4:2 | |
| 18.02.2023 | | 19. Jornada | Middlesbrough FC - Sunderland AFC | - | 0:2 | |
| 18.03.2023 | | 22. Jornada | Middlesbrough FC - Derby County | - | 1:0 | |
| 25.03.2023 | | 11. Jornada | Middlesbrough FC - Stoke City | - | 1:1 | |
| 08.04.2023 | | 4. Jornada | Middlesbrough FC - Manchester City | - | 1:2 | |
| 12.08.2023 | | 1. Jornada | Middlesbrough FC - Manchester United | - | 0:4 | |
| 19.08.2023 | | 24. Jornada | Middlesbrough FC - Nottingham Forest | - NOT | 1:1 | |
| 26.08.2023 | | 3. Jornada | Middlesbrough FC - Everton FC | - | 2:0 | |
| 16.09.2023 | | 4. Jornada | Middlesbrough FC - Manchester City | - | 0:6 | |
| 21.10.2023 |  | Grupo B | Middlesbrough FC - Arsenal FC | - | 0:1 | |
| 28.10.2023 | | 8. Jornada | Middlesbrough FC - Stoke City | - | 0:2 | |
| 17.11.2023 | | 10. Jornada | Middlesbrough FC - Derby County | - | 2:2 | |
| 25.11.2023 | | Grupo B | Middlesbrough FC - West Ham United | - | 1:5 |