Middlesbrough FC in the FA Cup
Competitions| 06-01-24 | Third Round | Aston Villa | Home | 0 | 1 |
| 07-01-23 | Third Round | Brighton | Home | 1 | 5 |
| 19-03-22 | Sixth Round | Chelsea | Home | 0 | 2 |
| 01-03-22 | Fifth Round | Tottenham Hotspur | Home | 1 | 0 |
| 04-02-22 | Fourth Round | Manchester United | Away | 1 | 1 |
| 08-01-22 | Third Round | Mansfield Town | Away | 3 | 2 |
| 09-01-21 | Third Round | Brentford | Away | 1 | 2 |
| 14-01-20 | Third Round Replay | Tottenham Hotspur | Away | 1 | 2 |
| 05-01-20 | Third Round | Tottenham Hotspur | Home | 1 | 1 |
| 05-02-19 | Fourth Round Replay | Newport County | Away | 0 | 2 |
| 26-01-19 | Fourth Round | Newport County | Home | 1 | 1 |
| 05-01-19 | Third Round | Peterborough United | Home | 5 | 0 |
| 27-01-18 | Fourth Round | Brighton | Home | 0 | 1 |
| 06-01-18 | Third Round | Sunderland | Home | 2 | 0 |
| 11-03-17 | Sixth Round | Manchester City | Home | 0 | 2 |
| 18-02-17 | Fifth Round | Oxford United | Home | 3 | 2 |
| 28-01-17 | Fourth Round | Accrington Stanley | Home | 1 | 0 |
| 08-01-17 | Third Round | Sheffield Wednesday | Home | 3 | 0 |
| 09-01-16 | Third Round | Burnley | Home | 1 | 2 |
| 05-02-15 | Fifth Round | Arsenal | Away | 0 | 2 |
| 24-01-15 | Fourth Round | Manchester City | Away | 2 | 0 |
| 03-01-15 | Third Round | Barnsley | Away | 2 | 0 |
| 04-01-14 | Third Round | Hull City | Home | 0 | 2 |
| 27-02-13 | Fifth Round | Chelsea | Home | 0 | 1 |
| 26-01-13 | Fourth Round | Aldershot | Home | 2 | 1 |
| 06-01-13 | Third Round | Hastings United | Home | 4 | 1 |
| 08-02-12 | Fourth Round Replay | Sunderland | Home | 1 | 2 |
| 29-01-12 | Fourth Round | Sunderland | Away | 1 | 1 |
| 07-01-12 | Third Round | Shrewsbury Town | Home | 1 | 0 |
| 08-01-11 | Third Round | Burton Albion | Away | 1 | 2 |
| 03-01-10 | Third Round | Manchester City | Home | 0 | 1 |
| 08-03-09 | Sixth Round | Everton | Away | 1 | 2 |
| 25-02-09 | Fifth Round Replay | West Ham United | Home | 2 | 0 |
| 14-02-09 | Fifth Round | West Ham United | Away | 1 | 1 |
| 24-01-09 | Fourth Round | Wolverhampton Wanderers | Away | 2 | 1 |
| 03-01-09 | Third Round | Barrow | Home | 2 | 1 |
| 08-03-08 | Sixth Round | Cardiff City | Home | 0 | 2 |
| 27-02-08 | Fifth Round Replay | Sheffield United | Home | 1 | 0 |
| 17-02-08 | Fifth Round | Sheffield United | Away | 0 | 0 |
| 26-01-08 | Fourth Round | Mansfield Town | Away | 2 | 0 |
| 05-01-08 | Third Round | Bristol City | Away | 2 | 1 |
| 19-03-07 | Sixth Round Replay | Manchester United | Away | 0 | 1 |
| 10-03-07 | Sixth Round | Manchester United | Home | 2 | 2 |
| 27-02-07 | Fifth Round Replay | West Bromwich Albion | Away | 1 | 1 |
| 17-02-07 | Fifth Round | West Bromwich Albion | Home | 2 | 2 |
| 13-02-07 | Fourth Round Replay | Bristol City | Home | 2 | 2 |
| 27-01-07 | Fourth Round | Bristol City | Away | 2 | 2 |
| 16-01-07 | Third Round Replay | Hull City | Home | 4 | 3 |
| 08-01-07 | Third Round | Hull City | Away | 1 | 1 |
| 23-04-06 | Semi Final | West Ham United | Neutral | 0 | 1 |