Head to Head
| Club Friendly List | 2016/07/09 11:30 | York v Middlesbrough | L | 0-6 |
Home History
| 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 |
| England National League North | 2020/12/08 19:45 | York v Kettering | W | 2-0 |
| England National League North | 2020/12/05 15:00 | York v Chester | W | 2-1 |
Away History
| England Championship | 2021/03/20 15:00 | Millwall v Middlesbrough | L | 1-0 |
| England Championship | 2021/03/16 19:00 | Middlesbrough v Preston | W | 2-0 |
| England Championship | 2021/03/13 15:00 | Middlesbrough v Stoke | W | 3-0 |
| England Championship | 2021/03/06 15:00 | Swansea v Middlesbrough | L | 2-1 |
| England Championship | 2021/03/02 19:00 | Coventry v Middlesbrough | W | 1-2 |
| England Championship | 2021/02/27 15:00 | Middlesbrough v Cardiff | D | 1-1 |
| England Championship | 2021/02/23 19:00 | Middlesbrough v Bristol City | L | 1-3 |
| England Championship | 2021/02/20 15:00 | Reading v Middlesbrough | W | 0-2 |
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