[11] Middlesbrough - U21 3-2 Manchester Utd - U21 [12] 2024-03-08 19:00
Stadium: Riverside Round: 16
Home History
| Anglia - Premier League 2 | 2024/03/01 19:00 | Norwich - U21 v Middlesbrough - U21 | W | 2-3 |
| Anglia - Premier League 2 | 2024/02/23 13:00 | Middlesbrough - U21 v Chelsea - U21 | L | 1-3 |
| Anglia - Premier League Cup - U21 | 2024/02/20 19:00 | Fulham - U21 v Middlesbrough - U21 | L | 2-1 |
| Anglia - Premier League 2 | 2024/02/16 19:00 | Aston Villa - U21 v Middlesbrough - U21 | L | 4-0 |
| Anglia - Premier League Cup - U21 | 2024/02/05 19:00 | Birmingham - U21 v Middlesbrough - U21 | W | 0-4 |
| Anglia - Premier League 2 | 2024/01/26 19:00 | Middlesbrough - U21 v West Brom - U21 | L | 0-1 |
| Anglia - Premier League Cup - U21 | 2024/01/23 19:00 | Ipswich - U21 v Middlesbrough - U21 | L | 2-0 |
| Anglia - Premier League 2 | 2024/01/12 19:00 | Arsenal - U21 v Middlesbrough - U21 | L | 1-0 |
Away History
| Anglia - Premier League 2 | 2024/03/01 19:00 | Manchester Utd - U21 v Derby - U21 | L | 2-4 |
| Anglia - Premier League 2 | 2024/02/19 19:00 | Manchester Utd - U21 v Manchester City - U21 | W | 2-1 |
| Anglia - Premier League 2 | 2024/01/27 15:00 | Manchester Utd - U21 v Norwich - U21 | W | 4-2 |
| Anglia - Premier League 2 | 2024/01/12 19:00 | Chelsea - U21 v Manchester Utd - U21 | L | 3-2 |
| Anglia - Premier League 2 | 2023/12/16 14:30 | Manchester Utd - U21 v Newcastle - U21 | W | 3-2 |
| Anglia - Premier League 2 | 2023/11/04 12:00 | Manchester Utd - U21 v Everton - U21 | W | 3-1 |
| Angol EFL Trophy | 2023/10/31 19:30 | Salford City v Manchester Utd - U21 | L | 4-3 |
| Anglia - Premier League 2 | 2023/10/27 18:00 | Fulham - U21 v Manchester Utd - U21 | D | 1-1 |