[7] Preston 0-2 Middlesbrough [16] 2020-01-01 15:00
Stadium: Deepdale Round: 26
Referee: John Brooks Home Manager: Alexander Francis Neil Away Manager: Jonathan Simon Woodgate
Head to Head
| England Championship | 2019/10/01 18:45 | Middlesbrough v Preston | D | 1-1 |
| England Championship | 2019/03/13 19:45 | Middlesbrough v Preston | W | 1-2 |
| England Championship | 2018/11/27 19:45 | Preston v Middlesbrough | D | 1-1 |
| England EFL Cup | 2018/09/25 18:45 | Preston v Middlesbrough | L | 5-6 |
| England Championship | 2018/01/01 15:00 | Preston v Middlesbrough | L | 2-3 |
| England Championship | 2017/08/26 14:00 | Middlesbrough v Preston | D | 0-0 |
| England Championship | 2016/04/09 14:00 | Middlesbrough v Preston | L | 1-0 |
| England Championship | 2015/08/09 11:00 | Preston v Middlesbrough | D | 0-0 |
| England EFL Cup | 2014/08/26 18:45 | Middlesbrough v Preston | L | 3-1 |