[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 |
Home History
| England - Championship | 2021/11/20 15:00 | Middlesbrough v Millwall | D | 1-1 |
| England - Championship | 2021/11/06 15:00 | West Brom v Middlesbrough | D | 1-1 |
| England - Championship | 2021/11/02 19:45 | Luton v Middlesbrough | L | 3-1 |
| England - Championship | 2021/10/30 14:00 | Middlesbrough v Birmingham | L | 0-2 |
| England - Championship | 2021/10/23 11:30 | Cardiff v Middlesbrough | W | 0-2 |
| England - Championship | 2021/10/20 18:45 | Middlesbrough v Barnsley | W | 2-0 |
| England - Championship | 2021/10/16 14:00 | Middlesbrough v Peterborough | W | 2-0 |
| England - Championship | 2021/10/02 14:00 | Hull v Middlesbrough | L | 2-0 |
Away History
| England - Championship | 2021/11/20 15:00 | Preston v Cardiff | L | 1-2 |
| England - Championship | 2021/11/06 15:00 | Nottm Forest v Preston | L | 3-0 |
| England - Championship | 2021/11/03 19:45 | Bournemouth v Preston | W | 1-2 |
| England - Championship | 2021/10/30 14:00 | Preston v Luton | W | 2-0 |
| England - EFL Cup | 2021/10/27 18:45 | Preston v Liverpool | L | 0-2 |
| England - Championship | 2021/10/23 14:00 | Blackpool v Preston | L | 2-0 |
| England - Championship | 2021/10/20 18:45 | Preston v Coventry | W | 2-1 |
| England - Championship | 2021/10/16 14:00 | Preston v Derby | D | 0-0 |