Head to Head
| Anglia - Premier League 2 | 2022/10/30 12:00 | Southampton - U21 v Middlesbrough - U21 | L | 8-1 |
Home History
| Anglia - Premier League 2 | 2023/01/09 19:00 | Sunderland - U21 v Middlesbrough - U21 | W | 5-7 |
| Anglia - Premier League Cup - U21 | 2023/01/05 14:00 | West Brom - U21 v Middlesbrough - U21 | W | 0-1 |
| Anglia - Premier League Cup - U21 | 2022/12/20 13:30 | Watford - U21 v Middlesbrough - U21 | L | 3-1 |
| Anglia - Premier League Cup - U21 | 2022/11/25 13:00 | Huddersfield - U21 v Middlesbrough - U21 | L | 2-0 |
| Anglia - Premier League Cup - U21 | 2022/11/19 11:00 | Middlesbrough - U21 v Watford - U21 | W | 4-0 |
| Anglia - Premier League 2 | 2022/10/30 12:00 | Southampton - U21 v Middlesbrough - U21 | L | 8-1 |
| Anglia - Premier League 2 | 2022/10/22 10:00 | Middlesbrough - U21 v Leeds - U21 | L | 2-4 |
| Anglia - Premier League Cup - U21 | 2022/10/17 17:00 | Middlesbrough - U21 v West Brom - U21 | W | 2-1 |
Away History
| Anglia - Premier League 2 | 2023/01/13 19:00 | Southampton - U21 v Newcastle - U21 | W | 4-1 |
| Anglia - Premier League 2 | 2023/01/06 19:00 | Southampton - U21 v Derby - U21 | W | 3-0 |
| Anglia - Premier League Cup - U21 | 2022/12/16 12:00 | Birmingham - U21 v Southampton - U21 | D | 2-2 |
| Anglia - Premier League Cup - U21 | 2022/12/02 19:00 | Southampton - U21 v Colchester - U21 | W | 7-1 |
| Anglia - Premier League Cup - U21 | 2022/11/26 13:00 | Colchester - U21 v Southampton - U21 | W | 0-5 |
| Anglia - Premier League Cup - U21 | 2022/11/21 19:00 | Southampton - U21 v Birmingham - U21 | W | 4-0 |
| Anglia - Premier League Cup - U21 | 2022/11/13 12:00 | Everton - U21 v Southampton - U21 | W | 1-2 |
| Anglia - Premier League 2 | 2022/11/07 13:00 | Sunderland - U21 v Southampton - U21 | W | 1-3 |
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