[20] Middlesbrough 1-0 Charlton [17] 2019-08-12 03:00
Stadium: Riverside Round: 20
Referee: Steve Martin Home Manager: Jonathan Simon Woodgate Away Manager: Lee Bowyer
Head to Head
| England Championship | 2016/03/13 15:30 | Charlton v Middlesbrough | L | 2-0 |
| England Championship | 2015/10/31 15:00 | Middlesbrough v Charlton | W | 3-0 |
| England Championship | 2015/02/07 15:00 | Middlesbrough v Charlton | W | 3-1 |
| England Championship | 2014/09/27 14:00 | Charlton v Middlesbrough | D | 0-0 |
Home History
| England Championship | 2019/08/10 14:00 | Middlesbrough v Brentford | L | 0-1 |
| England Championship | 2019/08/02 18:45 | Luton v Middlesbrough | D | 3-3 |
| Europe Friendlies | 2019/07/28 14:00 | Middlesbrough v St Etienne | D | 1-1 |
| Club Friendly List | 2019/07/23 18:30 | Salford City v Middlesbrough | W | 1-3 |
| Europe Friendlies | 2019/07/20 14:00 | Heidenheim v Middlesbrough | L | 5-1 |
| Club Friendly List | 2019/07/14 12:00 | Hartlepool v Middlesbrough | W | 0-4 |
| Club Friendly List | 2019/07/10 18:30 | Gateshead v Middlesbrough | W | 1-3 |
| Europe Friendlies | 2019/07/05 15:00 | Grazer AK v Middlesbrough | L | 2-0 |
Away History
| England Championship | 2019/08/10 14:00 | Charlton v Stoke | W | 3-1 |
| England Championship | 2019/08/03 14:00 | Blackburn v Charlton | W | 1-2 |
| Elite Club Friendlies | 2019/07/27 14:00 | Charlton v Aston Villa | L | 1-4 |
| Club Friendly List | 2019/07/23 18:30 | Colchester v Charlton | W | 1-2 |
| Club Friendly List | 2019/07/20 13:00 | Gillingham v Charlton | L | 3-1 |
| Club Friendly List | 2019/07/17 18:30 | Dag & Red v Charlton | W | 0-4 |
| Club Friendly List | 2019/07/16 18:30 | Ebbsfleet United v Charlton | L | 2-1 |
| Club Friendly List | 2019/07/13 14:00 | Welling v Charlton | W | 0-2 |