Stadium: Riverside Round: 3
Referee: Paul Tierney Home Manager: Chris Wilder Away Manager: Thomas Tuchel
| England Premier League | 2017/05/08 19:00 | Chelsea v Middlesbrough | L | 3-0 |
| England Premier League | 2016/11/20 16:00 | Middlesbrough v Chelsea | L | 0-1 |
| England FA Cup | 2022/03/01 19:55 | Middlesbrough v Tottenham | D | 0-0 |
| England Championship | 2022/02/26 15:00 | Barnsley v Middlesbrough | L | 3-2 |
| England Championship | 2022/02/22 19:45 | Middlesbrough v West Brom | W | 2-1 |
| England Championship | 2022/02/19 15:00 | Bristol City v Middlesbrough | L | 2-1 |
| England Championship | 2022/02/12 15:00 | Middlesbrough v Derby | W | 4-1 |
| England Championship | 2022/02/09 19:45 | QPR v Middlesbrough | D | 2-2 |
| England FA Cup | 2022/02/04 20:00 | Man Utd v Middlesbrough | D | 1-1 |
| England Championship | 2022/01/29 15:00 | Middlesbrough v Coventry | W | 1-0 |
| England FA Cup | 2022/03/02 19:15 | Luton v Chelsea | W | 2-3 |
| England EFL Cup | 2022/02/27 16:30 | Chelsea v Liverpool | D | 0-0 |
| UEFA Champions League | 2022/02/22 20:00 | Chelsea v Lille | W | 2-0 |
| England Premier League | 2022/02/19 15:00 | Crystal Palace v Chelsea | W | 0-1 |
| FIFA Club World Cup | 2022/02/12 16:30 | Chelsea v Palmeiras | D | 1-1 |
| FIFA Club World Cup | 2022/02/09 16:30 | Al Hilal Riyadh v Chelsea | W | 0-1 |
| England FA Cup | 2022/02/05 12:30 | Chelsea v Plymouth | D | 1-1 |
| England Premier League | 2022/01/23 16:30 | Chelsea v Tottenham | W | 2-0 |