Tottenham 2-1 Middlesbrough 2020-01-14 20:05
Stadion: Tottenham Hotspur Stadium Round: 9
Schiedsrichter: Craig Pawson Home Manager: Jose Mourinho Away Manager: Jonathan Woodgate
Head to Head
| England - FA Cup | 2020/01/05 14:01 | Middlesbrough v Tottenham | D | 1-1 |
| England - Premier League | 2017/02/04 17:30 | Tottenham v Middlesbrough | W | 1-0 |
| England - Premier League | 2016/09/24 14:00 | Middlesbrough v Tottenham | W | 1-2 |