Home History
| Anglia - Premier League 2 | 2024/03/08 19:00 | Middlesbrough - U21 v Manchester Utd - U21 | W | 3-2 |
| 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 |
Away History
| Anglia - Premier League 2 | 2024/03/08 19:00 | Arsenal - U21 v Tottenham - U21 | D | 1-1 |
| Anglia - Premier League 2 | 2024/03/02 13:00 | Tottenham - U21 v Everton - U21 | L | 1-2 |
| Anglia - Premier League Cup - U21 | 2024/02/24 13:00 | Tottenham - U21 v Fleetwood Town - U21 | W | 6-0 |
| Anglia - Premier League 2 | 2024/02/17 12:00 | Tottenham - U21 v West Ham - U21 | D | 1-1 |
| Anglia - Premier League Cup - U21 | 2024/02/03 13:00 | Tottenham - U21 v Peterborough - U21 | L | 0-3 |
| Anglia - Premier League Cup - U21 | 2024/01/30 19:00 | Tottenham - U21 v Bristol City - U21 | W | 1-0 |
| Anglia - Premier League 2 | 2024/01/27 13:00 | Tottenham - U21 v Aston Villa - U21 | W | 5-3 |
| Anglia - Premier League 2 | 2024/01/12 19:00 | Southampton - U21 v Tottenham - U21 | W | 2-3 |
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