Head to Head
| Club Friendly List | 2022/07/08 18:00 | York v Middlesbrough | L | 2-3 |
| Club Friendly List | 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 FA Trophy | 2023/02/11 15:00 | Southend v York | W | 0-2 |
| England National League | 2023/02/07 19:45 | York v Solihull Moors | L | 2-3 |
| England National League | 2023/02/04 15:00 | Southend v York | L | 2-0 |
| England National League | 2023/01/28 15:00 | York v Maidenhead Utd | L | 1-2 |
| England National League | 2023/01/24 19:45 | Oldham v York | L | 2-0 |
| England FA Trophy | 2023/01/14 15:00 | York v Chelmsford | D | 1-1 |
| England National League | 2023/01/07 15:00 | York v Maidstone Utd | W | 4-1 |
| England National League | 2023/01/02 15:00 | Gateshead v York | D | 2-2 |
Away History
| England Championship | 2023/02/15 20:00 | Sheff Utd v Middlesbrough | W | 1-3 |
| England Championship | 2023/02/11 15:00 | Cardiff v Middlesbrough | W | 1-3 |
| England Championship | 2023/02/04 15:00 | Middlesbrough v Blackpool | W | 3-0 |
| England Championship | 2023/01/28 15:00 | Middlesbrough v Watford | W | 2-0 |
| England Championship | 2023/01/22 12:00 | Sunderland v Middlesbrough | L | 2-0 |
| England Championship | 2023/01/14 15:00 | Middlesbrough v Millwall | W | 1-0 |
| England FA Cup | 2023/01/07 15:00 | Middlesbrough v Brighton | L | 1-5 |
| England Championship | 2023/01/02 15:00 | Birmingham v Middlesbrough | W | 1-3 |
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