Liverpool will take on League Two side Carlisle United in the League Cup 3rd Round following the draw last night.
Carlisle United, struggling near the foot of the Football League, were surprise victors away at Championship side QPR last night.
The Cumbrians connection with Liverpool can be traced back to the Shankly era - Bill Shankly famously played for and later began his managerial career at Carlisle.
Geoff Twentyman, a Liverpool signing from Carlisle, became a key scout for the reds after his playing career - unearthing the likes of Ian Rush (£300k), Phil Neal (£66k) and Alan Hansen (£100k).
Many of Carlisle's supporters have the reds as their second club and the draw has been greeted with excitement at the northern end of the M6 motorway.
The clubs last met in 1989 in that season's ill fated FA Cup. The third round cup tie was held at Brunton Park with Liverpool winning 3-0 thanks to goals from John Barnes and a brace from Steve McMahon.
The last meeting at Anfield was almost 39 years ago - in the FA Cup 4th Round. Keegan, Heighway and Toshack helping Bob Paisley's team to a 3-0 win.
The clubs have only met in the League Cup once before, in 1972. A 1-1 draw at Brunton Park forced an Anfield replay which Bill Shankly's Liverpool won comprehensively 5-1.
Carlisle United have had ownership concerns in recent times. A recent bid from a local business consortium was rejected by the current owners early this summer - who then announced there was interest from a mysterious 'billionaire'. The clearly shy and retiring 'billionaire' has not yet been revealed by club owners John Nixon and Andrew Jenkins.
Full Draw
Middlesbrough v Wolves
Norwich City v West Brom or Port Vale
Hull City v Swansea
Leicester City v West Ham
Aston Villa v Birmingham
Tottenham v Arsenal
Manchester United v Ipswich Town
Liverpool v Carlisle United
Crystal Palace v Charlton Athletic
Fulham v Stoke City
Sunderland v Manchester City
Newcastle United v Sheffield Wednesday
Reading v Barnsley or Everton
Preston v Bournemouth
Walsall v Chelsea
Milton Keynes Dons v Southampton