[13] Middlesbrough 0-1 Brentford [20] 2019-08-10 14:00
Stadium: Riverside Round: 2
Referee: Steve Martin Home Manager: Jonathan Simon Woodgate Away Manager: Thomas Frank
Head to Head
| England Championship | 2019/03/09 15:00 | Middlesbrough v Brentford | L | 1-2 |
| England Championship | 2018/11/24 17:30 | Brentford v Middlesbrough | W | 1-2 |
| England Championship | 2018/03/17 15:00 | Brentford v Middlesbrough | D | 1-1 |
| England Championship | 2017/09/30 14:00 | Middlesbrough v Brentford | D | 2-2 |
| England Championship | 2016/01/12 19:45 | Brentford v Middlesbrough | W | 0-1 |
| England Championship | 2015/09/15 18:45 | Middlesbrough v Brentford | W | 3-1 |
| England Championship | 2015/05/15 18:45 | Middlesbrough v Brentford | W | 3-0 |
| England Championship | 2015/05/08 18:45 | Brentford v Middlesbrough | W | 1-2 |
Home History
| 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 |
| England Championship | 2019/05/05 11:30 | Rotherham v Middlesbrough | W | 1-2 |
Away History
| England Championship | 2019/08/03 14:00 | Brentford v Birmingham | L | 0-1 |
| Elite Club Friendlies | 2019/07/27 14:00 | Brentford v Bournemouth | L | 1-3 |
| Club Friendly List | 2019/07/24 15:30 | Norwich v Brentford | W | 1-3 |
| Club Friendly List | 2019/07/20 14:00 | Wycombe v Brentford | D | 2-2 |
| Europe Friendlies | 2019/07/13 10:00 | Dynamo Kiev v Brentford | D | 0-0 |
| Club Friendly List | 2019/07/05 18:45 | AFC Wimbledon v Brentford | W | 0-3 |
| England Championship | 2019/05/05 11:30 | Brentford v Preston | W | 3-0 |
| England Championship | 2019/04/27 14:00 | Bolton v Brentford | W | 0-1 |