Home History
| England Premier League 2 | 2021/11/29 19:00 | Reading U23 v Middlesbrough U23 | L | 2-1 |
| England Premier League 2 | 2021/11/21 13:00 | Middlesbrough U23 v Norwich U23 | W | 3-2 |
| England U23 Premier League Cup | 2021/11/12 19:00 | Middlesbrough U23 v Nottm Forest U23 | W | 2-1 |
| England Premier League 2 | 2021/11/07 13:00 | Middlesbrough U23 v Birmingham U23 | L | 0-3 |
| England Premier League 2 | 2021/11/01 14:00 | Fulham U23 v Middlesbrough U23 | L | 2-0 |
| England Premier League 2 | 2021/10/22 18:00 | Burnley U23 v Middlesbrough U23 | L | 2-0 |
| England Premier League 2 | 2021/10/17 12:00 | Middlesbrough U23 v West Brom U23 | L | 1-2 |
| England U23 Premier League Cup | 2021/10/08 18:00 | Blackburn U23 v Middlesbrough U23 | L | 3-2 |
Away History
| England Premier League 2 | 2021/11/26 19:00 | Arsenal U23 v Derby U23 | L | 3-5 |
| England Premier League 2 | 2021/11/22 19:00 | Blackburn U23 v Arsenal U23 | W | 2-3 |
| England U23 Premier League Cup | 2021/11/11 19:00 | Arsenal U23 v West Brom U23 | L | 1-4 |
| England Premier League 2 | 2021/11/06 13:00 | Arsenal U23 v Leicester U23 | D | 3-3 |
| England Premier League 2 | 2021/10/29 18:00 | Leeds U23 v Arsenal U23 | W | 2-4 |
| England Premier League 2 | 2021/10/22 18:00 | Arsenal U23 v Everton U23 | W | 4-0 |
| England Premier League 2 | 2021/10/16 15:00 | Liverpool U23 v Arsenal U23 | L | 3-0 |
| England U23 Premier League Cup | 2021/10/06 18:00 | Bournemouth U23 v Arsenal U23 | D | 1-1 |