Middlesbrough 4-6 Crewe 2019-08-13 18:45
Stadium: Riverside Round: 7
Referee: Michael Salisbury Home Manager: Jonathan Simon Woodgate Away Manager: David Artell
Home History
| England - Championship | 2019/08/10 14:00 | Middlesbrough v Brentford | L | 0-1 |
| England - Championship | 2019/08/02 18:45 | Luton v Middlesbrough | D | 3-3 |
| Europa - Vennskapskamper | 2019/07/28 14:00 | Middlesbrough v St Etienne | D | 1-1 |
| Europa - Vennskapskamper | 2019/07/23 18:30 | Salford City v Middlesbrough | W | 1-3 |
| Europa - Vennskapskamper | 2019/07/20 14:00 | Heidenheim v Middlesbrough | L | 5-1 |
| Europa - Vennskapskamper | 2019/07/14 12:00 | Hartlepool v Middlesbrough | W | 0-4 |
| Europa - Vennskapskamper | 2019/07/10 18:30 | Gateshead v Middlesbrough | W | 1-3 |
| Europa - Vennskapskamper | 2019/07/05 15:00 | Grazer AK v Middlesbrough | L | 2-0 |
Away History
| England - League 2 | 2019/08/10 14:00 | Oldham v Crewe | W | 1-2 |
| England - League 2 | 2019/08/03 14:00 | Crewe v Plymouth | L | 0-3 |
| Europa - Vennskapskamper | 2019/07/27 14:00 | Wrexham v Crewe | W | 0-1 |
| Europa - Vennskapskamper | 2019/07/23 18:45 | Bala Town v Crewe | W | 2-5 |
| Storbritannia - Vennskapskamper | 2019/07/20 14:02 | Crewe v Burnley XI | W | 1-0 |
| Europa - Vennskapskamper | 2019/07/20 14:00 | Crewe v Burnley | W | 1-0 |
| Europa - Vennskapskamper | 2019/07/16 18:45 | Curzon Ashton v Crewe | W | 1-5 |
| Europa - Vennskapskamper | 2019/07/16 18:45 | Witton Albion v Crewe | W | 0-3 |