Middlesbrough FC in the League Cup
Competitions| 27-08-24 | Second Round | Stoke City | Home | 0 | 5 |
| 14-08-24 | First Round | Leeds United | Away | 3 | 0 |
| 23-01-24 | Semi Final 2nd Leg | Chelsea | Away | 1 | 6 |
| 09-01-24 | Semi Final 1st Leg | Chelsea | Home | 1 | 0 |
| 19-12-23 | Fifth Round | Port Vale | Away | 3 | 0 |
| 01-11-23 | Fourth Round | Exeter City | Away | 3 | 2 |
| 26-09-23 | Third Round | Bradford City | Away | 2 | 0 |
| 29-08-23 | Second Round | Bolton Wanderers | Away | 3 | 1 |
| 08-08-23 | First Round | Huddersfield Town | Away | 3 | 2 |
| 10-08-22 | First Round | Barnsley | Home | 0 | 1 |
| 11-08-21 | First Round | Blackpool | Away | 0 | 3 |
| 15-09-20 | Second Round | Barnsley | Home | 0 | 2 |
| 04-09-20 | First Round | Shrewsbury Town | Home | 4 | 3 |
| 13-08-19 | First Round | Crewe Alexandra | Home | 2 | 2 |
| 18-12-18 | Fifth Round | Burton Albion | Home | 0 | 1 |
| 31-10-18 | Fourth Round | Crystal Palace | Home | 1 | 0 |
| 25-09-18 | Third Round | Preston North End | Away | 2 | 2 |
| 28-08-18 | Second Round | Rochdale | Home | 2 | 1 |
| 14-08-18 | First Round | Notts County | Home | 3 | 3 |
| 24-10-17 | Third Round | Bournemouth | Away | 1 | 3 |
| 19-09-17 | Second Round | Aston Villa | Away | 2 | 0 |
| 22-08-17 | First Round | Scunthorpe United | Home | 3 | 0 |
| 22-08-16 | Second Round | Fulham | Away | 1 | 2 |
| 01-12-15 | Fifth Round | Everton | Home | 0 | 1 |
| 28-10-15 | Fourth Round | Manchester United | Away | 0 | 0 |
| 22-09-15 | Third Round | Wolverhampton Wanderers | Home | 3 | 0 |
| 25-08-15 | Second Round | Burton Albion | Away | 2 | 1 |
| 12-08-15 | First Round | Oldham Athletic | Away | 3 | 1 |
| 23-09-14 | Third Round | Liverpool | Away | 2 | 2 |
| 26-08-14 | Second Leg | Preston North End | Home | 3 | 1 |
| 12-08-14 | First Round | Oldham Athletic | Away | 3 | 0 |
| 06-08-13 | First Round | Accrington Stanley | Home | 1 | 2 |
| 12-12-12 | Fifth Round | Swansea City | Away | 0 | 1 |
| 30-10-12 | Fourth Round | Sunderland | Away | 1 | 0 |
| 25-09-12 | Third Round | Preston North End | Away | 3 | 1 |
| 28-08-12 | Second Round | Gillingham | Away | 2 | 0 |
| 11-08-12 | First Round | Bury | Away | 2 | 1 |
| 20-09-11 | Third Round | Crystal Palace | Away | 1 | 2 |
| 24-08-11 | Second Round | Peterborough United | Away | 2 | 0 |
| 09-08-11 | First Round | Walsall | Away | 3 | 0 |
| 24-08-10 | Second Round | Millwall | Away | 1 | 2 |
| 10-08-10 | First Round | Chesterfield | Away | 2 | 1 |
| 25-08-09 | Second Round | Nottingham Forest | Away | 1 | 2 |
| 23-09-08 | Third Round | Manchester United | Away | 1 | 3 |
| 26-08-08 | Second Round | Yeovil Town | Home | 5 | 1 |
| 26-09-07 | Third Round | Tottenham Hotspur | Away | 0 | 2 |
| 29-08-07 | Second Round | Northampton Town | Home | 2 | 0 |
| 20-09-06 | Second Round | Notts County | Away | 0 | 1 |
| 21-12-05 | Fifth Round | Blackburn Rovers | Home | 0 | 1 |
| 30-11-05 | Fourth Round | Crystal Palace | Home | 2 | 1 |