Middlesbrough : News
| 29.11.2025 | ECHS | Middlesbrough | 2:1 | Derby County |
| 05.12.2025 | ECHS | Hull City | 1:4 | Middlesbrough |
| 09.12.2025 | ECHS | Charlton | -:- | Middlesbrough |
| 13.12.2025 | ECHS | Middlesbrough | -:- | Queens Park Rangers |
| 20.12.2025 | ECHS | Bristol City | -:- | Middlesbrough |
| 1. | Coventry | 13 | 4 | 2 | 43 |
| 2. | Middlesbrough | 10 | 6 | 3 | 36 |
| 3. | Millwall | 10 | 4 | 5 | 34 |
| 4. | Ipswich Town | 8 | 7 | 4 | 31 |
| 5. | Preston North End | 8 | 7 | 4 | 31 |
The match at the Riverside Stadium saw drama unfold early
Chelsea left no chance for Middlesbrough in the English League Cup semi-final match, a total defeat
Chelsea have not yet been knocked out of the League Cup, but have taken a step towards it
Tottenham has officially announced the signing of Djed Spence from Middlesbrough
