Plan de juego
| Fecha | Ronda | Partido | Partido | Res. | Espectadores | |
|---|---|---|---|---|---|---|
| 12.01.2019 |  | 13. Jornada | Middlesbrough FC - West Bromwich Albion | - | 5:3 | |
| 19.01.2019 | | 14. Jornada | Middlesbrough FC - Everton FC | - | 3:2 | |
| 23.02.2019 | | 16. Jornada | Middlesbrough FC - Derby County | - | 0:2 | |
| 20.03.2019 | | 8. Jornada | Middlesbrough FC - Blackburn Rovers | - | 2:2 | |
| 23.03.2019 | | 19. Jornada | Middlesbrough FC - Manchester City | - | 4:2 | |
| 13.04.2019 | | 21. Jornada | Middlesbrough FC - Newcastle United | - | 4:1 | |
| 24.04.2019 | | 18. Jornada | Middlesbrough FC - Wolverhampton Wanderers | - | 2:1 | |
| 23.08.2019 |  | 3. Jornada | Middlesb. U21 - Swansea U23 | - | 3:2 | 70 |
| 24.08.2019 | | 3. Jornada | Middlesbrough FC - Manchester City | - | 1:3 | |
| 14.09.2019 | | 5. Jornada | Middlesbrough FC - Wolverhampton Wanderers | - | 2:0 | |
| 28.09.2019 |  | Grupo B | Middlesbrough FC - Aston Villa | - | 2:3 | |
| 05.10.2019 | | 7. Jornada | Middlesbrough FC - Stoke City | - | 1:1 | |
| 02.11.2019 | | 9. Jornada | Middlesbrough FC - Sunderland AFC | - | 4:3 | |
| 23.11.2019 | | Grupo B | Middlesbrough FC - Reading FC | - | 0:0 | |
| 06.12.2019 | | 11. Jornada | Middlesbrough FC - West Bromwich Albion | - | 3:2 |