[16] Middlesbrough 2-1 Bristol City [11] 2021-08-14 14:00
Stadium: Riverside Round: 2
Referee: Oliver Langford Home Manager: Neil Warnock Away Manager: Nigel Pearson
Head to Head
| England Championship | 2021/02/23 19:00 | Middlesbrough v Bristol City | L | 1-3 |
| England Championship | 2020/10/20 18:45 | Bristol City v Middlesbrough | W | 0-1 |
| England Championship | 2020/07/11 14:00 | Middlesbrough v Bristol City | L | 1-3 |
| England Championship | 2019/08/31 11:30 | Bristol City v Middlesbrough | D | 2-2 |
| England Championship | 2019/04/02 18:45 | Middlesbrough v Bristol City | L | 0-1 |
| England Championship | 2018/08/18 14:00 | Bristol City v Middlesbrough | W | 0-2 |
| England Championship | 2018/04/14 14:00 | Middlesbrough v Bristol City | W | 2-1 |
| England Championship | 2017/12/02 17:30 | Bristol City v Middlesbrough | L | 2-1 |
Home History
| England EFL Cup | 2021/08/11 18:45 | Blackpool v Middlesbrough | L | 3-0 |
| England Championship | 2021/08/08 12:30 | Fulham v Middlesbrough | D | 1-1 |
| Club Friendly List | 2021/07/30 18:00 | Rotherham v Middlesbrough | W | 0-1 |
| World Club Friendlies | 2021/07/27 18:00 | York v Middlesbrough | L | 2-1 |
| World Club Friendlies | 2021/07/23 18:00 | Plymouth v Middlesbrough | W | 1-2 |
| Club Friendly List | 2021/07/21 18:00 | Tavistock v Middlesbrough | W | 0-7 |
| England Championship | 2021/05/08 11:30 | Middlesbrough v Wycombe | L | 0-3 |
| England Championship | 2021/05/01 14:00 | Luton v Middlesbrough | D | 1-1 |
Away History
| England EFL Cup | 2021/08/10 18:45 | Forest Green v Bristol City | L | 8-7 |
| England Championship | 2021/08/07 14:00 | Bristol City v Blackpool | D | 1-1 |
| Elite Club Friendlies | 2021/07/31 12:00 | Bristol City v Aston Villa | L | 0-3 |
| Club Friendly List | 2021/07/27 17:00 | Plymouth v Bristol City | W | 0-1 |
| Club Friendly List | 2021/07/27 12:00 | Exeter v Bristol City | W | 0-4 |
| World Club Friendlies | 2021/07/24 12:30 | Bristol City v Milton Keynes Dons | W | 3-1 |
| Club Friendly List | 2021/07/20 13:00 | Bristol City v Portsmouth | D | 3-3 |
| Club Friendly List | 2021/07/14 18:45 | Bristol City v Celtic | D | 0-0 |