Head to Head
| 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
| England National League North | 2022/05/21 14:00 | York v Boston Utd | W | 2-0 |
| England National League North | 2022/05/14 14:00 | Brackley v York | W | 0-1 |
| England National League North | 2022/05/11 18:45 | York v Chorley | W | 2-1 |
| England National League North | 2022/05/07 14:00 | AFC Telford v York | D | 1-1 |
| England National League North | 2022/05/02 14:00 | York v AFC Fylde | W | 2-1 |
| England National League North | 2022/04/30 14:00 | Farsley Celtic v York | W | 0-2 |
| England National League North | 2022/04/26 18:45 | Chester v York | W | 0-1 |
| England National League North | 2022/04/23 14:00 | York v Gloucester | D | 1-1 |
Away History
| Club Friendly List | 2022/07/02 12:00 | Bishop Auckland v Middlesbrough | W | 0-5 |
| England Championship | 2022/05/07 11:30 | Preston v Middlesbrough | L | 4-1 |
| England Championship | 2022/04/30 14:00 | Middlesbrough v Stoke | W | 3-1 |
| England Championship | 2022/04/27 18:45 | Middlesbrough v Cardiff | W | 2-0 |
| England Championship | 2022/04/23 14:00 | Swansea v Middlesbrough | D | 1-1 |
| England Championship | 2022/04/18 11:30 | Middlesbrough v Huddersfield | L | 0-2 |
| England Championship | 2022/04/15 14:00 | Bournemouth v Middlesbrough | D | 0-0 |
| England Championship | 2022/04/09 14:00 | Middlesbrough v Hull | L | 0-1 |