Reds to face BoroUnited will host Middlesbrough at Old Trafford in the Third Round of the Carling Cup.
The tie will take place in the week commencing 22 September, 2008.
The clubs have met six times before in the League Cup, with United triumphing three times and two matches ending in draws. Boro's sole win arrived at Old Trafford in October 1973.
The last time the sides met in the competition was at the semi-final stage in 1992. The teams played out a 0-0 draw at Ayresome Park before United won the second leg 2-1 at Old Trafford.
Elsewhere, Portsmouth will host Chelsea, Crewe Alexandra face a trip to Liverpool and Swansea meet Cardiff in an all-Welsh tie.
Carling Cup Third Round
Arsenal v Sheffield United
Brighton & Hove or Man City v Derby
Burnley v Fulham
Portsmouth v Chelsea
Blackburn Rovers v Everton
Rotherham United v Southampton
Swansea City v Cardiff City
Ipswich Town v Wigan Athletic
Stoke City v Reading
Leeds United v Hartlepool United
Watford v West Ham United
Manchester United v Middlesbrough
Liverpool v Crewe Alexandra
Aston Villa v Queens Park Rangers
Sunderland v Northampton Town
Newcastle United v Tottenham Hotspur