Middlesbrough FC in the League Cup
Competitions| 26-10-05 | Third Round | Everton | Away | 1 | 0 |
| 10-11-04 | Fourth Round | Liverpool | Away | 0 | 2 |
| 27-10-04 | Third Round | Coventry City | Home | 3 | 0 |
| 29-02-04 | Final | Bolton Wanderers | Neutral | 2 | 1 |
| 03-02-04 | Semi Final 2nd Leg | Arsenal | Home | 2 | 1 |
| 20-01-04 | Semi Final 1st Leg | Arsenal | Away | 1 | 0 |
| 17-12-03 | Fifth Round | Tottenham Hotspur | Away | 1 | 1 |
| 03-12-03 | Fourth Round | Everton | Home | 0 | 0 |
| 29-10-03 | Third Round | Wigan Athletic | Away | 2 | 1 |
| 24-09-03 | Second Round | Brighton | Home | 1 | 0 |
| 06-11-02 | Third Round | Ipswich Town | Away | 1 | 3 |
| 01-10-02 | Second Round | Brentford | Away | 4 | 1 |
| 10-10-01 | Third Round | Blackburn Rovers | Away | 1 | 2 |
| 11-09-01 | Second Round | Northampton Town | Home | 3 | 1 |
| 31-10-00 | Fourth Round | Wimbledon | Away | 0 | 1 |
| 26-09-00 | Second Round 2nd Leg | Macclesfield Town | Away | 3 | 1 |
| 19-09-00 | Second Round 1st Leg | Macclesfield Town | Home | 2 | 1 |
| 14-12-99 | Fifth Round | Tranmere Rovers | Away | 1 | 2 |
| 30-11-99 | Fourth Round | Arsenal | Home | 2 | 2 |
| 13-10-99 | Third Round | Watford | Home | 1 | 0 |
| 21-09-99 | Second Round 2nd Leg | Chesterfield | Home | 2 | 1 |
| 14-09-99 | Second Round 1st Leg | Chesterfield | Away | 0 | 0 |
| 28-10-98 | Third Round | Everton | Home | 2 | 3 |
| 22-09-98 | Second Round 2nd Leg | Wycombe Wanderers | Away | 1 | 1 |
| 16-09-98 | Second Round 1st Leg | Wycombe Wanderers | Home | 2 | 0 |
| 29-03-98 | Final | Chelsea | Neutral | 0 | 2 |
| 18-02-98 | Semi Final 2nd Leg | Liverpool | Home | 2 | 0 |
| 27-01-98 | Semi Final 1st Leg | Liverpool | Away | 1 | 2 |
| 06-01-98 | Fifth Round | Reading | Away | 1 | 0 |
| 18-11-97 | Fourth Round | Bolton Wanderers | Home | 2 | 1 |
| 15-10-97 | Third Round | Sunderland | Home | 2 | 0 |
| 23-09-97 | Second Round 2nd Leg | Barnet | Away | 2 | 0 |
| 16-09-97 | Second Round 1st Leg | Barnet | Home | 1 | 0 |
| 16-04-97 | Final Replay | Leicester City | Neutral | 0 | 1 |
| 06-04-97 | Final | Leicester City | Neutral | 1 | 1 |
| 12-03-97 | Semi Final 2nd Leg | Stockport County | Home | 0 | 1 |
| 26-02-97 | Semi Final 1st Leg | Stockport County | Away | 2 | 0 |
| 08-01-97 | Fifth Round | Liverpool | Home | 2 | 1 |
| 27-11-96 | Fourth Round | Newcastle United | Home | 3 | 1 |
| 23-10-96 | Third Round | Huddersfield Town | Home | 5 | 1 |
| 24-09-96 | Second Round 2nd Leg | Hereford United | Away | 3 | 0 |
| 18-09-96 | Second Round 1st Leg | Hereford United | Home | 7 | 0 |
| 20-12-95 | Fourth Round Replay | Birmingham City | Away | 0 | 2 |
| 29-11-95 | Fourth Round | Birmingham City | Home | 0 | 0 |
| 08-11-95 | Third Round Replay | Crystal Palace | Home | 2 | 0 |
| 25-10-95 | Third Round | Crystal Palace | Away | 2 | 2 |
| 03-10-95 | Second Round 2nd Leg | Rotherham United | Away | 1 | 0 |
| 20-09-95 | Second Round 1st Leg | Rotherham United | Home | 2 | 1 |
| 26-10-94 | Third Round | Aston Villa | Away | 0 | 1 |
| 27-09-94 | Second Round 2nd Leg | Scarborough | Home | 4 | 1 |