[23] Sheff Wednesday 2-1 Middlesbrough [8] 2020-12-29 19:00
Stadion: Hillsborough Stadium Round: 22
Schiedsrichter: Geoff Eltringham Home Manager: Tony Pulis Away Manager: Neil Warnock
Head to Head
| England - Championship | 2020/07/22 18:30 | Sheff Wednesday v Middlesbrough | L | 1-2 |
| England - Championship | 2019/09/28 14:00 | Middlesbrough v Sheff Wednesday | W | 1-4 |
| England - Championship | 2018/12/26 15:00 | Middlesbrough v Sheff Wednesday | W | 0-1 |
| England - Championship | 2018/10/19 18:45 | Sheff Wednesday v Middlesbrough | L | 1-2 |
| England - Championship | 2018/01/30 19:45 | Middlesbrough v Sheff Wednesday | D | 0-0 |
| England - Championship | 2017/12/23 15:00 | Sheff Wednesday v Middlesbrough | L | 1-2 |
| England - FA Cup | 2017/01/08 15:00 | Middlesbrough v Sheff Wednesday | L | 3-0 |
| England - Championship | 2015/12/28 17:15 | Middlesbrough v Sheff Wednesday | L | 1-0 |
| England - Championship | 2015/08/29 14:00 | Sheff Wednesday v Middlesbrough | L | 1-3 |
| England - Championship | 2015/02/28 15:00 | Sheff Wednesday v Middlesbrough | W | 2-0 |
| England - Championship | 2014/08/23 14:00 | Middlesbrough v Sheff Wednesday | W | 2-3 |