[14] Middlesbrough 1-2 Preston [16] 2021-11-23 19:45
Stadium: Riverside Round: 19
Referee: Andy Woolmer Home Manager: Chris Wilder Away Manager: Frankie McAvoy
Head to Head
| England Championship | 2021/03/16 19:00 | Middlesbrough v Preston | W | 2-0 |
| England Championship | 2020/12/09 19:00 | Preston v Middlesbrough | L | 3-0 |
| England Championship | 2020/01/01 15:00 | Preston v Middlesbrough | W | 0-2 |
| England Championship | 2019/10/01 18:45 | Middlesbrough v Preston | D | 1-1 |
| England Championship | 2019/03/13 19:45 | Middlesbrough v Preston | L | 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 | W | 5-6 |
| England Championship | 2018/01/01 15:00 | Preston v Middlesbrough | W | 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 | W | 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 | W | 3-1 |