Stadium: Riverside Round: 19
Referee: Andy Davies Home Manager: Neil Warnock Away Manager: Nathan Jones
| England Championship | 2020/02/15 15:00 | Middlesbrough v Luton | L | 0-1 |
| England Championship | 2019/08/02 18:45 | Luton v Middlesbrough | D | 3-3 |
| England Championship | 2020/11/07 15:00 | Brentford v Middlesbrough | D | 0-0 |
| England Championship | 2020/11/03 19:45 | Blackburn v Middlesbrough | D | 0-0 |
| England Championship | 2020/10/31 15:00 | Middlesbrough v Nottm Forest | W | 1-0 |
| England Championship | 2020/10/27 19:45 | Middlesbrough v Coventry | W | 2-0 |
| England Championship | 2020/10/24 14:00 | Cardiff v Middlesbrough | D | 1-1 |
| England Championship | 2020/10/20 18:45 | Bristol City v Middlesbrough | W | 0-1 |
| England Championship | 2020/10/17 14:00 | Middlesbrough v Reading | D | 0-0 |
| England Championship | 2020/10/03 14:00 | Middlesbrough v Barnsley | W | 2-1 |
| England Championship | 2020/11/07 15:00 | Huddersfield v Luton | D | 1-1 |
| England Championship | 2020/11/04 19:45 | Rotherham v Luton | W | 0-1 |
| England Championship | 2020/10/31 15:00 | Luton v Brentford | L | 0-3 |
| England Championship | 2020/10/28 19:45 | Luton v Nottm Forest | D | 1-1 |
| England Championship | 2020/10/24 14:00 | Sheff Wed v Luton | W | 0-1 |
| England Championship | 2020/10/20 18:45 | Millwall v Luton | L | 2-0 |
| England Championship | 2020/10/17 14:00 | Luton v Stoke | L | 0-2 |
| England Championship | 2020/10/03 14:00 | Luton v Wycombe | W | 2-0 |