Head to Head
| Club Friendly List | 2016/07/09 11:30 | York v Middlesbrough | L | 0-6 |
Home History
| Club Friendly List | 2021/07/21 18:00 | York v Sunderland | D | 1-1 |
| World Club Friendlies | 2021/07/18 13:00 | York v Newcastle | W | 1-0 |
| England National League North | 2021/02/16 19:00 | York v AFC Fylde | L | 1-3 |
| England National League North | 2021/01/05 19:45 | Kidderminster v York | D | 2-2 |
| England National League North | 2020/12/28 15:00 | York v Guiseley | W | 1-0 |
| England National League North | 2020/12/26 15:00 | Bradford P A v York | L | 4-2 |
| England FA Trophy | 2020/12/15 19:45 | Ashton Utd v York | L | 7-5 |
| England National League North | 2020/12/12 15:00 | York v Spennymoor Town | D | 1-1 |
Away History
| World Club Friendlies | 2021/07/23 18:00 | Plymouth v Middlesbrough | W | 1-2 |
| Club Friendly List | 2021/07/21 18:00 | Tavistock v Middlesbrough | W | 0-7 |
| England Championship | 2021/05/08 11:30 | Middlesbrough v Wycombe | L | 0-3 |
| England Championship | 2021/05/01 14:00 | Luton v Middlesbrough | D | 1-1 |
| England Championship | 2021/04/24 14:00 | Middlesbrough v Sheff Wed | W | 3-1 |
| England Championship | 2021/04/21 17:00 | Rotherham v Middlesbrough | W | 1-2 |
| England Championship | 2021/04/17 11:30 | Middlesbrough v QPR | L | 1-2 |
| England Championship | 2021/04/10 14:00 | Barnsley v Middlesbrough | L | 2-0 |