| 14h00 |   Chelsea U21 vs Middlesbrough U21 | 1 - 0 | Premier League 2 Division One
Phase : 8e de finale | Kingsmeadow |
| 19h00 |  Aston Villa U21 vs Middlesbrough U21 | 0 - 2 | Premier League 2 Division One
Phase : J21 | Bodymoor Heath Training Ground |
| 20h00 |  Scunthorpe vs Middlesbrough U21 | 3 - 2 | National League Cup
Groupe stage
Phase : Phase de groupes J4 | Arène Attis |
| 16h00 |  Brighton U21 vs Middlesbrough U21 | 1 - 1 | Premier League 2 Division One
Phase : J6 | Elite Football Performance Centre |
