[18] Middlesbrough 0-1 Monopoli U19 [23] 2020-01-27 11:00
Stadium: Riverside Round: 33
Referee: Jarred Gillett Home Manager: Jonathan Simon Woodgate Away Manager: Graeme Anthony Jones
Head to Head
| England Championship | 2019/08/02 18:45 | Luton v Middlesbrough | D | 3-3 |
Home History
| England Championship | 2020/01/21 19:45 | Middlesbrough v Birmingham | D | 1-1 |
| England Championship | 2020/01/17 19:45 | Fulham v Middlesbrough | L | 1-0 |
| England FA Cup | 2020/01/14 20:05 | Tottenham v Middlesbrough | L | 2-1 |
| England Championship | 2020/01/11 15:00 | Middlesbrough v Derby | D | 2-2 |
| England FA Cup | 2020/01/05 14:01 | Middlesbrough v Tottenham | D | 1-1 |
| England Championship | 2020/01/01 15:00 | Preston v Middlesbrough | W | 0-2 |
| 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 |
Away History
| England Championship | 2020/01/19 12:00 | Nottm Forest v Luton | L | 3-1 |
| England Championship | 2020/01/11 15:00 | Luton v Birmingham | L | 1-2 |
| England FA Cup | 2020/01/04 17:31 | Bournemouth v Luton | L | 4-0 |
| England Championship | 2020/01/01 12:45 | Millwall v Luton | L | 3-1 |
| England Championship | 2019/12/29 15:00 | Bristol City v Luton | L | 3-0 |
| England Championship | 2019/12/26 15:00 | Luton v Fulham | D | 3-3 |
| England Championship | 2019/12/21 15:00 | Luton v Swansea | L | 0-1 |
| England Championship | 2019/12/14 15:00 | Preston v Luton | L | 2-1 |
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