[7] Middlesbrough U23 1-2 Southampton U23 [3] 2019-01-13 13:00
Weather: Windy Stadium: Riverside Pitch: Good Round: 1
Head to Head
| England Premier League 2 | 2018/08/10 18:00 | Southampton U23 v Middlesbrough U23 | L | 2-0 |
| England Premier League 2 | 2018/04/23 18:00 | Southampton U23 v Middlesbrough U23 | L | 2-1 |
| England Premier League 2 | 2017/11/26 13:00 | Middlesbrough U23 v Southampton U23 | D | 3-3 |
Home History
| England Premier League 2 | 2019/01/04 13:00 | Fulham U23 v Middlesbrough U23 | D | 2-2 |
| England Premier League 2 | 2018/12/14 19:00 | Middlesbrough U23 v West Brom U23 | D | 2-2 |
| England Premier League 2 | 2018/12/07 19:00 | Man Utd U23 v Middlesbrough U23 | L | 2-0 |
| England Premier League 2 | 2018/11/26 19:00 | Sunderland U23 v Middlesbrough U23 | W | 1-3 |
| England Premier League 2 | 2018/11/04 13:00 | Middlesbrough U23 v Norwich U23 | W | 2-1 |
| England Premier League 2 | 2018/10/26 18:00 | Newcastle U23 v Middlesbrough U23 | W | 1-3 |
| England Premier League 2 | 2018/10/19 18:00 | Middlesbrough U23 v Reading U23 | L | 2-3 |
| England Premier League 2 | 2018/09/28 18:00 | Wolverhampton U23 v Middlesbrough U23 | L | 2-0 |
Away History
| England Premier League 2 | 2019/01/04 19:00 | Southampton U23 v Stoke U23 | W | 2-0 |
| England Premier League 2 | 2018/12/14 19:00 | Southampton U23 v Newcastle U23 | W | 2-1 |
| England Premier League 2 | 2018/12/07 19:00 | Aston Villa U23 v Southampton U23 | L | 2-1 |
| England U23 Premier League Cup | 2018/11/28 13:58 | Notts County U23 v Southampton U23 | W | 0-7 |
| England U23 Premier League Cup | 2018/11/09 19:00 | Southampton U23 v Newcastle U23 | D | 1-1 |
| England Premier League 2 | 2018/11/02 19:00 | Southampton U23 v West Brom U23 | W | 1-0 |
| England Premier League 2 | 2018/10/28 12:30 | Sunderland U23 v Southampton U23 | W | 0-2 |
| England Premier League 2 | 2018/10/19 18:00 | Southampton U23 v Wolverhampton U23 | W | 3-2 |