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