Head to Head
| Club Friendly List | 2022/07/08 18:00 | York v Middlesbrough | L | 2-3 |
| World Club Friendlies | 2021/07/27 18:00 | York v Middlesbrough | W | 2-1 |
| Club Friendly List | 2016/07/09 11:30 | York v Middlesbrough | L | 0-6 |
Home History
| Club Friendly List | 2023/07/08 12:30 | York v Sheff Wed | D | 1-1 |
| England National League | 2023/04/29 16:30 | Notts County v York | D | 1-1 |
| England National League | 2023/04/22 14:00 | York v Aldershot | D | 2-2 |
| England National League | 2023/04/15 14:00 | Torquay v York | L | 3-2 |
| England National League | 2023/04/10 14:00 | York v Halifax | L | 0-3 |
| England National League | 2023/04/07 14:00 | Chesterfield v York | W | 1-3 |
| England National League | 2023/04/03 18:45 | York v Barnet | W | 1-0 |
| England National League | 2023/03/28 18:45 | York v Scunthorpe | D | 0-0 |
Away History
| Club Friendly List | 2023/07/14 18:00 | Hartlepool v Middlesbrough | L | 2-1 |
| Club Friendly List | 2023/07/08 12:00 | Guimaraes v Middlesbrough | W | 0-1 |
| England Championship | 2023/05/17 19:00 | Middlesbrough v Coventry | L | 0-1 |
| England Championship | 2023/05/14 11:00 | Coventry v Middlesbrough | D | 0-0 |
| England Championship | 2023/05/08 14:00 | Middlesbrough v Coventry | D | 1-1 |
| England Championship | 2023/05/01 12:00 | Rotherham v Middlesbrough | L | 1-0 |
| England Championship | 2023/04/24 19:00 | Luton v Middlesbrough | L | 2-1 |
| England Championship | 2023/04/19 19:00 | Middlesbrough v Hull | W | 3-1 |