Middlesbrough FC in the League Cup
Competitions| 20-09-94 | Second Round 1st Leg | Scarborough | Away | 4 | 1 |
| 10-11-93 | Third Round Replay | Sheffield Wednesday | Away | 1 | 2 |
| 27-10-93 | Third Round | Sheffield Wednesday | Home | 1 | 1 |
| 06-10-93 | Second Round 2nd Leg | Brighton | Away | 3 | 1 |
| 21-09-93 | Second Round 1st Leg | Brighton | Home | 5 | 0 |
| 07-10-92 | Second Round 2nd Leg | Newcastle United | Home | 1 | 3 |
| 23-09-92 | Second Round 1st Leg | Newcastle United | Away | 0 | 0 |
| 11-03-92 | Semi Final 2nd Leg | Manchester United | Away | 1 | 2 |
| 04-03-92 | Semi Final 1st Leg | Manchester United | Home | 0 | 0 |
| 12-02-92 | Fifth Round Replay | Peterborough United | Home | 1 | 0 |
| 08-01-92 | Fifth Round | Peterborough United | Away | 0 | 0 |
| 03-12-91 | Fourth Round | Manchester City | Home | 2 | 1 |
| 29-10-91 | Third Round | Barnsley | Home | 1 | 0 |
| 08-10-91 | Second Round 2nd Leg | Bournemouth | Away | 2 | 1 |
| 24-09-91 | Second Round 1st Leg | Bournemouth | Home | 1 | 1 |
| 28-11-90 | Fourth Round | Aston Villa | Away | 2 | 3 |
| 30-10-90 | Third Round | Norwich City | Home | 2 | 0 |
| 10-10-90 | Second Round 2nd Leg | Newcastle United | Away | 0 | 1 |
| 25-09-90 | Second Round 1st Leg | Newcastle United | Home | 2 | 0 |
| 03-09-90 | First Round 2nd Leg | Tranmere Rovers | Away | 2 | 1 |
| 28-08-90 | First Round 1st Leg | Tranmere Rovers | Home | 1 | 1 |
| 08-11-89 | Second Round 2nd Leg | Wimbledon | Away | 0 | 1 |
| 25-10-89 | Second Round 1st Leg | Wimbledon | Home | 1 | 1 |
| 03-10-89 | First Round 2nd Leg | Halifax Town | Away | 1 | 0 |
| 20-09-89 | First Round 1st Leg | Halifax Town | Home | 4 | 0 |
| 11-10-88 | Second Round 2nd Leg | Tranmere Rovers | Away | 0 | 1 |
| 28-09-88 | Second Round 1st Leg | Tranmere Rovers | Home | 0 | 0 |
| 07-10-87 | Second Round 2nd Leg | Aston Villa | Home | 0 | 1 |
| 23-09-87 | Second Round 1st Leg | Aston Villa | Away | 0 | 1 |
| 25-08-87 | First Round 2nd Leg | Sunderland | Away | 0 | 1 |
| 18-08-87 | First Round 1st Leg | Sunderland | Home | 2 | 0 |
| 07-10-86 | Second Round 2nd Leg | Birmingham City | Away | 2 | 3 |
| 23-09-86 | Second Round 1st Leg | Birmingham City | Home | 2 | 2 |
| 02-09-86 | First Round 2nd Leg | Hartlepool United | Home | 2 | 0 |
| 26-08-86 | First Round 1st Leg | Hartlepool United | Away | 1 | 1 |
| 03-09-85 | Second Round 2nd Leg | Mansfield Town | Home | 4 | 4 |
| 21-08-85 | Second Round 1st Leg | Mansfield Town | Away | 0 | 2 |
| 04-09-84 | First Round 2nd Leg | Bradford City | Home | 2 | 2 |
| 29-08-84 | First Round 1st Leg | Bradford City | Away | 0 | 2 |
| 13-09-83 | First Round 2nd Leg | Chesterfield | Away | 1 | 0 |
| 30-08-83 | First Round 1st Leg | Chesterfield | Home | 0 | 1 |
| 26-10-82 | First Round 2nd Leg | Burnley | Home | 1 | 1 |
| 05-10-82 | First Round 1st Leg | Burnley | Away | 2 | 3 |
| 10-11-81 | Second Round | Liverpool | Away | 1 | 4 |
| 27-10-81 | First Round 2nd Leg | Plymouth Argyle | Away | 0 | 0 |
| 06-10-81 | First Round 1st Leg | Plymouth Argyle | Home | 2 | 1 |
| 02-09-80 | Second Round 2nd Leg | Ipswich Town | Away | 0 | 3 |
| 26-08-80 | Second Round 1st Leg | Ipswich Town | Home | 3 | 1 |
| 25-09-79 | Third Round | Nottingham Forest | Home | 1 | 3 |
| 04-09-79 | Second Round 2nd Leg | Derby County | Home | 1 | 1 |