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Liverpool v Middlesbrough
| Liverpool Win | Liverpool Draw | Liverpool Defeat |
| Season | Competition | Round | Club | Home | Away | Venue | Other Info |
| 1974/1975 | League Cup | 4th Round | Middlesbrough | 0-1 | |||
| 1976/1977 | FA Cup | Quarter Final | Middlesbrough | 2-0 | |||
| 1981/1982 | League Cup | 3rd Round | Middlesbrough | 4-1 | |||
| 1996/1997 | League Cup | Quarter Final | Middlesbrough | 1-2 | |||
| 1997/1998 | League Cup | Semi Final | Middlesbrough | 2-1 | 1st Leg | ||
| 1997/1998 | League Cup | Semi Final | Middlesbrough | 0-2 | 2nd Leg | ||
| 2004/2005 | League Cup | 4th Round | Middlesbrough | 2-0 |
Liverpool v Middlesbrough in League Matches
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Opponents: Middlesbrough