Head to Head
| England Premier League 2 | 2023/09/03 13:00 | Liverpool U21 v Middlesbrough U21 | L | 1-4 |
Home History
| England Premier League 2 | 2025/02/16 14:00 | Liverpool U21 v Chelsea U21 | L | 0-3 |
| England Premier League 2 | 2025/02/07 19:00 | Southampton U21 v Liverpool U21 | D | 1-1 |
| England Premier League 2 | 2025/01/26 13:00 | Tottenham U21 v Liverpool U21 | L | 2-0 |
| England Premier League 2 | 2025/01/18 14:00 | Liverpool U21 v West Brom U21 | L | 0-5 |
| Premier League International Cup | 2025/01/15 19:00 | Liverpool U21 v Sparta Prague U21 | L | 1-3 |
| England Premier League 2 | 2024/12/16 12:00 | Crystal Palace U21 v Liverpool U21 | D | 3-3 |
| Premier League International Cup | 2024/12/04 19:00 | Liverpool U21 v FC Nordsjaelland U21 | L | 3-4 |
| England Premier League 2 | 2024/11/30 12:00 | Reading U21 v Liverpool U21 | D | 1-1 |
Away History
| England Premier League 2 | 2025/02/14 19:00 | Arsenal U21 v Middlesbrough U21 | L | 2-1 |
| England Premier League 2 | 2025/02/10 19:00 | Fulham U21 v Middlesbrough U21 | L | 2-0 |
| England National League Cup | 2025/01/28 19:45 | Tamworth v Middlesbrough U21 | W | 0-2 |
| England National League Cup | 2025/01/21 19:30 | Boston Utd v Middlesbrough U21 | D | 1-1 |
| England Premier League 2 | 2025/01/17 19:00 | Blackburn U21 v Middlesbrough U21 | L | 3-2 |
| Premier League International Cup | 2025/01/14 19:00 | Middlesbrough U21 v Athletic Bilbao U21 | L | 0-4 |
| Premier League International Cup | 2024/12/18 19:00 | Middlesbrough U21 v Benfica U21 | L | 0-1 |
| England Premier League 2 | 2024/12/13 19:00 | Norwich U21 v Middlesbrough U21 | W | 1-3 |