[15] Middlesbrough 1-4 Sheff Wednesday [10] 2019-09-28 14:00
Stadion: Riverside Round: 9
Schiedsrichter: James Linington Home Manager: Jonathan Woodgate Away Manager: Garry Monk
Head to Head
| England - Championship | 2018/12/26 15:00 | Middlesbrough v Sheff Wednesday | L | 0-1 |
| England - Championship | 2018/10/19 18:45 | Sheff Wednesday v Middlesbrough | W | 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 | W | 1-2 |
| England - FA Cup | 2017/01/08 15:00 | Middlesbrough v Sheff Wednesday | W | 3-0 |
| England - Championship | 2015/12/28 17:15 | Middlesbrough v Sheff Wednesday | W | 1-0 |
| England - Championship | 2015/08/29 14:00 | Sheff Wednesday v Middlesbrough | W | 1-3 |
| England - Championship | 2015/02/28 15:00 | Sheff Wednesday v Middlesbrough | L | 2-0 |
Home History
| England - Championship | 2019/09/21 14:00 | Cardiff v Middlesbrough | L | 1-0 |
| England - Championship | 2019/09/14 14:00 | Middlesbrough v Reading | W | 1-0 |
| England - Championship | 2019/08/31 11:30 | Bristol City v Middlesbrough | D | 2-2 |
| England - Championship | 2019/08/24 14:00 | Middlesbrough v Millwall | D | 1-1 |
| England - Championship | 2019/08/20 18:45 | Middlesbrough v Wigan | W | 1-0 |
| England - Championship | 2019/08/17 14:00 | Blackburn v Middlesbrough | L | 1-0 |
| England - EFL Cup | 2019/08/13 18:45 | Middlesbrough v Crewe | L | 4-6 |
| England - Championship | 2019/08/10 14:00 | Middlesbrough v Brentford | L | 0-1 |
Away History
| England - EFL Cup | 2019/09/24 18:45 | Sheff Wednesday v Everton | L | 0-2 |
| England - Championship | 2019/09/21 14:00 | Sheff Wednesday v Fulham | D | 1-1 |
| England - Championship | 2019/09/15 11:00 | Huddersfield v Sheff Wednesday | W | 0-2 |
| England - Championship | 2019/08/31 14:00 | Sheff Wednesday v Queens Park Rangers | L | 1-2 |
| England - EFL Cup | 2019/08/28 18:45 | Rotherham v Sheff Wednesday | W | 0-1 |
| England - Championship | 2019/08/24 14:00 | Preston v Sheff Wednesday | L | 2-1 |
| England - Championship | 2019/08/20 18:45 | Sheff Wednesday v Luton | W | 1-0 |
| England - Championship | 2019/08/17 14:00 | Millwall v Sheff Wednesday | L | 1-0 |