25/04 - 20:00
| h2h | 2022-03-19 | Middlesbrough |  | 0-2 |  | Chelsea | QF | |||
| h2h | 2018-10-31 | Middlesbrough | | 1-0 |  | Crystal Palace | 4R | |||
| h2h | 2018-04-28 | Middlesbrough | | 2-0 |  | Millwall | D45 | |||
| h2h | 2017-09-30 | Middlesbrough | | 2-2 |  | Brentford | D11 | |||
| h2h | 2015-11-03 | Middlesbrough | | 1-0 |  | Rotherham | D15 | |||
| h2h | 2015-08-22 | Middlesbrough | | 0-1 |  | Bristol City | D4 | |||
| h2h | 2014-09-30 | Middlesbrough | | 1-1 |  | Blackpool | D10 | |||
| h2h | 2013-12-29 | Middlesbrough | | 3-0 |  | Reading | D23 | |||
| h2h | 2013-11-09 | Middlesbrough | | 2-2 |  | Watford | D15 | |||
| h2h | 2013-08-10 | Charlton Athletic |  | 0-1 | | Middlesbrough | D2 |
| h2h | 2024-04-06 | Crystal Palace | | 2-4 |  | Manchester City | D32 | |||
| h2h | 2024-02-19 | Everton |  | 1-1 | | Crystal Palace | D25 | |||
| h2h | 2024-01-20 | Arsenal |  | 5-0 | | Crystal Palace | D21 | |||
| h2h | 2023-12-16 | Manchester City | | 2-2 | | Crystal Palace | D17 | |||
| h2h | 2023-09-23 | Crystal Palace | | 0-0 |  | Fulham | D6 | |||
| h2h | 2023-02-18 | Brentford | | 1-1 | | Crystal Palace | D24 | |||
| h2h | 2022-11-06 | West Ham |  | 1-2 | | Crystal Palace | D15 | |||
| h2h | 2022-10-09 | Crystal Palace | | 2-1 |  | Leeds United | D10 | |||
| h2h | 2022-08-15 | Liverpool |  | 1-1 | | Crystal Palace | D2 | |||
| h2h | 2022-04-04 | Crystal Palace | | 3-0 | | Arsenal | D31 |
