| 2024-05-04 13:30 | J46 | Middlesbrough |  | - |  | Watford | | FF |
| 2024-04-22 21:00 | J44 | Middlesbrough | | 3-4 |  | Leeds United | Isaiah Jones 7', Latte Lath 30' 87'; Crys Summerville 14' (p.) 61', Patrick Bamford 18', Willy Gnonto 39' | |
| 2024-04-06 16:00 | J41 | Middlesbrough | | 2-0 |  | Swansea City | Latte Lath 45' 79' | |
| 2024-04-01 16:00 | J40 | Middlesbrough | | 2-0 |  | Sheffield Wed. | Isaiah Jones 73'; Michael Ihiekwe 41' (p.p.) | |
| 2024-03-16 16:00 | J38 | Middlesbrough | | 0-0 |  | Blackburn Rovers | | |
| 2024-03-06 20:45 | J36 | Middlesbrough | | 3-1 |  | Norwich City | Marcus Forss 37', Latte Lath 43', Lukas Engel 62'; Ashley Barnes 17' | |
| 2024-02-24 16:00 | J34 | Middlesbrough | | 0-2 |  | Plymouth Argyle | Matty Sorinola 7', Ryan Hardie 31' | |
| 2024-02-10 16:00 | J31 | Middlesbrough | | 1-2 |  | Bristol City | Sam Silvera 90'; Jason Knight 16', Matty James 17' | |
| 2024-02-04 13:00 | J30 | Middlesbrough | | 1-1 |  | Sunderland | Marcus Forss 61'; Nazariy Rusyn 83' | |
| 2024-01-20 16:00 | J28 | Middlesbrough | | 1-1 |  | Rotherham | Marcus Forss 82'; Cafú 59' | |
| 2024-01-09 21:00 | SF | Middlesbrough | | 1-0 |  | Chelsea | Hayden Hackney 37' | |
| 2024-01-06 18:30 | 3R | Middlesbrough | | 0-1 |  | Aston Villa | Matty Cash 87' | |
| 2024-01-01 16:00 | J26 | Middlesbrough | | 1-3 |  | Coventry City | Josh Coburn 31'; Tatsuhiro Sakamoto 34' 69', Haji Wright 58' | |
| 2023-12-23 16:00 | J23 | Middlesbrough | | 1-0 |  | West Bromwich | Morgan Rogers 40' | |
| 2023-12-13 21:00 | J21 | Middlesbrough | | 1-2 |  | Hull City | Latte Lath 6'; Liam Delap 69', Ozan Tufan 82' | |
| 2023-12-09 16:00 | J20 | Middlesbrough | | 0-2 |  | Ipswich Town | Conor Chaplin 36', Omari Hutchinson 67' | |
| 2023-11-28 20:45 | J18 | Middlesbrough | | 4-0 |  | Preston North End | Isaiah Jones 16' 37', Rav van den Berg 26', Alex Bangura 90' | |
| 2023-11-11 16:00 | J16 | Middlesbrough | | 1-0 |  | Leicester City | Sam Greenwood 83' | |
| 2023-10-28 16:00 | J14 | Middlesbrough | | 0-2 |  | Stoke City | Michael Rose 8', Mehdi Léris 37' | |
| 2023-10-21 16:00 | J12 | Middlesbrough | | 1-0 |  | Birmingham City | Morgan Rogers 88' | |
| 2023-10-03 20:45 | J10 | Middlesbrough | | 2-0 |  | Cardiff City | Isaiah Jones 56', Latte Lath 84' | |
| 2023-09-23 16:00 | J8 | Middlesbrough | | 2-1 |  | Southampton | Riley McGree 44', Jonny Howson 66' (p.); Adam Armstrong 17' | |
| 2023-09-02 16:00 | J5 | Middlesbrough | | 0-2 |  | QPR | Andre Dozzell 43', Jack Colback 71' | |
| 2023-08-19 16:00 | J3 | Middlesbrough | | 1-1 |  | Huddersfield Town | Dael Fry 47' (p.p.), Hayden Hackney 61' | |
| 2023-08-05 16:00 | J1 | Middlesbrough | | 0-1 |  | Millwall | Romain Esse 79' | |
