Gameplan
| Date | Round | Match | Match | Res. | Attendance | |
|---|---|---|---|---|---|---|
| 14.01.2023 |  | Matchday 15 | Middlesbrough FC - Nottingham Forest | - NOT | 0:4 | |
| 27.01.2023 |  | Matchday 14 | Middlesb. U21 - Southampt. U21 | - | 2:2 | 50 |
| 28.01.2023 | | Matchday 17 | Middlesbrough FC - Liverpool FC | - | 4:2 | |
| 18.02.2023 | | Matchday 19 | Middlesbrough FC - Sunderland AFC | - | 0:2 | |
| 18.03.2023 | | Matchday 22 | Middlesbrough FC - Derby County | - | 1:0 | |
| 25.03.2023 | | Matchday 11 | Middlesbrough FC - Stoke City | - | 1:1 | |
| 08.04.2023 | | Matchday 4 | Middlesbrough FC - Manchester City | - | 1:2 | |
| 12.08.2023 | | Matchday 1 | Middlesbrough FC - Manchester United | - | 0:4 | |
| 19.08.2023 | | Matchday 24 | Middlesbrough FC - Nottingham Forest | - NOT | 1:1 | |
| 26.08.2023 | | Matchday 3 | Middlesbrough FC - Everton FC | - | 2:0 | |
| 16.09.2023 | | Matchday 4 | Middlesbrough FC - Manchester City | - | 0:6 | |
| 21.10.2023 |  | Group B | Middlesbrough FC - Arsenal FC | - | 0:1 | |
| 28.10.2023 | | Matchday 8 | Middlesbrough FC - Stoke City | - | 0:2 | |
| 17.11.2023 | | Matchday 10 | Middlesbrough FC - Derby County | - | 2:2 | |
| 25.11.2023 | | Group B | Middlesbrough FC - West Ham United | - | 1:5 |