Barnsley host United in League Cup
The other second-tier sides still in the competition get away ties, with Darren Ferguson's Peterborough travelling to Blackburn while Scunthorpe visit moneybags Manchester City.
The most eye-catching tie for TV moguls may be Arsenal against Liverpool, although Arsene Wenger will be playing his youth side and Rafa Benitez will probably also pick a shadow squad.
The hardest-fought tie may well be Spurs against Everton – two sides just outside the Big Four who may fancy a full tilt at silverware.
Ties will be played in the week starting October 26.
Blackburn Rovers v Peterborough United Manchester City v Scunthorpe United Tottenham Hotspur v Everton Barnsley v Manchester United Chelsea v Bolton Wanderers Sunderland v Aston Villa Arsenal v Liverpool Portsmouth v Stoke City