[17] Middlesbrough Sub21 3-2 Wolverhampton Sub21 [24] 2023-08-25 18:00
Estádio: Estádio Riverside Round: 3
Home History
| Inglaterra - Premier League 2 | 2023/08/18 18:00 | Middlesbrough Sub21 v Everton Sub21 | D | 2-2 |
| Inglaterra - Premier League 2 | 2023/08/14 18:00 | Nottm Forest Sub21 v Middlesbrough Sub21 | D | 2-2 |
| Inglaterra - Premier League 2 | 2023/04/23 13:00 | Leeds Sub21 v Middlesbrough Sub21 | L | 3-1 |
| Inglaterra - Premier League 2 | 2023/04/14 18:00 | Middlesbrough Sub21 v Nottm Forest Sub21 | L | 0-1 |
| Inglaterra - Premier League 2 | 2023/04/03 18:00 | Newcastle Sub21 v Middlesbrough Sub21 | D | 0-0 |
| Inglaterra - Premier League 2 | 2023/03/24 14:00 | Derby Sub21 v Middlesbrough Sub21 | W | 1-5 |
| Inglaterra - Premier League 2 | 2023/03/06 19:00 | Middlesbrough Sub21 v Aston Villa Sub21 | L | 2-3 |
| Inglaterra - Premier League 2 | 2023/02/24 12:00 | Norwich Sub21 v Middlesbrough Sub21 | D | 2-2 |
Away History
| Inglaterra - Premier League 2 | 2023/08/21 18:00 | Stoke Sub21 v Wolverhampton Sub21 | L | 2-1 |
| Inglaterra - Premier League 2 | 2023/08/11 18:00 | Wolverhampton Sub21 v Fulham Sub21 | L | 2-3 |
| Inglaterra - Premier League 2 | 2023/04/29 12:00 | Man City Sub21 v Wolverhampton Sub21 | L | 4-3 |
| Inglaterra - Premier League 2 | 2023/04/24 18:00 | Wolverhampton Sub21 v Crystal Palace Sub21 | W | 5-0 |
| Inglaterra - Premier League 2 | 2023/04/17 18:00 | Fulham Sub21 v Wolverhampton Sub21 | L | 2-1 |
| Inglaterra - Premier League 2 | 2023/04/10 18:00 | Wolverhampton Sub21 v Everton Sub21 | W | 5-0 |
| Inglaterra - Premier League 2 | 2023/04/07 12:00 | Tottenham Sub21 v Wolverhampton Sub21 | D | 1-1 |
| Inglaterra - Premier League 2 | 2023/03/31 18:00 | Everton Sub21 v Wolverhampton Sub21 | L | 3-0 |