Stadium: St Andrew's Trillion Trophy Stadium Round: 34
Referee: Graham Scott Home Manager: Mark Robins Away Manager: Neil Warnock
| England Championship | 2020/10/27 19:45 | Middlesbrough v Coventry | L | 2-0 |
| England Championship | 2021/02/02 19:00 | Coventry v Nottm Forest | L | 1-2 |
| England Championship | 2021/01/30 15:00 | Birmingham v Coventry | D | 1-1 |
| England Championship | 2021/01/27 19:00 | Coventry v Sheff Wed | W | 2-0 |
| England Championship | 2021/01/19 18:00 | Reading v Coventry | L | 3-0 |
| England FA Cup | 2021/01/09 12:00 | Norwich v Coventry | L | 2-0 |
| England Championship | 2021/01/02 15:00 | Millwall v Coventry | W | 1-2 |
| England Championship | 2020/12/29 19:45 | Preston v Coventry | L | 2-0 |
| England Championship | 2020/12/26 15:00 | Coventry v Stoke | D | 0-0 |
| England Championship | 2021/01/30 12:30 | Norwich v Middlesbrough | D | 0-0 |
| England Championship | 2021/01/27 19:00 | Middlesbrough v Rotherham | L | 0-3 |
| England Championship | 2021/01/24 15:00 | Middlesbrough v Blackburn | L | 0-1 |
| England Championship | 2021/01/20 19:00 | Nottm Forest v Middlesbrough | W | 1-2 |
| England Championship | 2021/01/16 12:30 | Middlesbrough v Birmingham | L | 0-1 |
| England FA Cup | 2021/01/09 18:00 | Brentford v Middlesbrough | L | 2-1 |
| England Championship | 2021/01/02 15:00 | Wycombe v Middlesbrough | W | 1-3 |
| England Championship | 2020/12/29 19:00 | Sheff Wed v Middlesbrough | L | 2-1 |