Home History
| England Premier League 2 | 2023/12/18 19:00 | Sunderland U21 v Arsenal U21 | W | 1-2 |
| England EFL Trophy | 2023/12/05 19:30 | Peterborough v Arsenal U21 | L | 3-0 |
| England EFL Trophy | 2023/11/14 19:00 | Reading v Arsenal U21 | L | 5-2 |
| England Premier League 2 | 2023/11/03 19:00 | Arsenal U21 v Man City U21 | D | 3-3 |
| England Premier League 2 | 2023/10/29 14:00 | Arsenal U21 v Brighton U21 | W | 6-3 |
| England EFL Trophy | 2023/10/10 18:15 | Exeter v Arsenal U21 | W | 0-5 |
| England Premier League 2 | 2023/09/29 18:00 | Everton U21 v Arsenal U21 | D | 1-1 |
| England Premier League 2 | 2023/09/23 11:00 | Man Utd U21 v Arsenal U21 | W | 2-4 |
Away History
| England Premier League 2 | 2023/12/18 19:00 | Reading U21 v Middlesbrough U21 | D | 2-2 |
| England U21 Premier League Cup | 2023/12/11 19:00 | Crystal Palace U21 v Middlesbrough U21 | W | 0-4 |
| England U21 Premier League Cup | 2023/11/12 12:00 | Middlesbrough U21 v Birmingham U21 | L | 0-2 |
| England Premier League 2 | 2023/11/05 13:00 | Middlesbrough U21 v Derby U21 | W | 1-0 |
| England Premier League 2 | 2023/10/27 18:00 | West Ham U21 v Middlesbrough U21 | L | 5-0 |
| England U21 Premier League Cup | 2023/10/06 18:00 | Middlesbrough U21 v Ipswich U21 | W | 2-0 |
| England Premier League 2 | 2023/09/29 18:00 | Middlesbrough U21 v Stoke U21 | W | 4-1 |
| England Premier League 2 | 2023/09/25 18:00 | Leicester U21 v Middlesbrough U21 | W | 1-3 |