[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 |
Home History
| England Championship | 2019/12/29 15:00 | Preston v Reading | L | 0-2 |
| England Championship | 2019/12/26 17:15 | Leeds v Preston | D | 1-1 |
| England Championship | 2019/12/21 12:30 | Cardiff v Preston | D | 0-0 |
| England Championship | 2019/12/14 15:00 | Preston v Luton | W | 2-1 |
| England Championship | 2019/12/10 19:45 | Preston v Fulham | W | 2-1 |
| England Championship | 2019/12/07 15:00 | QPR v Preston | L | 2-0 |
| England Championship | 2019/12/02 19:45 | Preston v West Brom | L | 0-1 |
| England Championship | 2019/11/27 19:45 | Hull v Preston | L | 4-0 |
Away History
| England Championship | 2019/12/29 15:00 | West Brom v Middlesbrough | W | 0-2 |
| England Championship | 2019/12/26 15:00 | Middlesbrough v Huddersfield | W | 1-0 |
| England Championship | 2019/12/20 19:45 | Middlesbrough v Stoke | W | 2-1 |
| England Championship | 2019/12/14 15:00 | Swansea v Middlesbrough | L | 3-1 |
| England Championship | 2019/12/10 19:45 | Nottm Forest v Middlesbrough | D | 1-1 |
| England Championship | 2019/12/07 15:00 | Middlesbrough v Charlton | W | 1-0 |
| England Championship | 2019/11/30 15:00 | Leeds v Middlesbrough | L | 4-0 |
| England Championship | 2019/11/27 19:45 | Middlesbrough v Barnsley | W | 1-0 |