[9] Reading - U21 2-2 Middlesbrough - U21 [5] 2023-12-18 19:00
Stadium: Select Car Leasing Stadium Round: 10
Home History
| Anglia - Premier League 2 | 2023/12/04 19:00 | Derby - U21 v Reading - U21 | L | 5-1 |
| Anglia - Premier League Cup - U21 | 2023/11/13 19:00 | Reading - U21 v West Brom - U21 | L | 2-3 |
| Anglia - Premier League 2 | 2023/11/06 18:00 | West Brom - U21 v Reading - U21 | D | 0-0 |
| Anglia - Premier League 2 | 2023/10/30 19:00 | Reading - U21 v Blackburn - U21 | W | 7-2 |
| Anglia - Premier League Cup - U21 | 2023/10/09 18:00 | Sheff Utd - U21 v Reading - U21 | D | 2-2 |
| Anglia - Premier League 2 | 2023/09/29 18:00 | Southampton - U21 v Reading - U21 | L | 6-0 |
| Anglia - Premier League 2 | 2023/09/22 18:00 | Reading - U21 v Leeds - U21 | W | 3-2 |
| Anglia - Premier League Cup - U21 | 2023/09/11 18:00 | Reading - U21 v Blackburn - U21 | L | 1-2 |
Away History
| Anglia - Premier League Cup - U21 | 2023/12/11 19:00 | Crystal Palace - U21 v Middlesbrough - U21 | W | 0-4 |
| Anglia - Premier League Cup - U21 | 2023/11/12 12:00 | Middlesbrough - U21 v Birmingham - U21 | L | 0-2 |
| Anglia - Premier League 2 | 2023/11/05 13:00 | Middlesbrough - U21 v Derby - U21 | W | 1-0 |
| Anglia - Premier League 2 | 2023/10/27 18:00 | West Ham - U21 v Middlesbrough - U21 | L | 5-0 |
| Anglia - Premier League Cup - U21 | 2023/10/06 18:00 | Middlesbrough - U21 v Ipswich - U21 | W | 2-0 |
| Anglia - Premier League 2 | 2023/09/29 18:00 | Middlesbrough - U21 v Stoke - U21 | W | 4-1 |
| Anglia - Premier League 2 | 2023/09/25 18:00 | Leicester - U21 v Middlesbrough - U21 | W | 1-3 |
| Anglia - Premier League Cup - U21 | 2023/09/15 18:00 | Middlesbrough - U21 v Crystal Palace - U21 | L | 2-6 |