Arsenal have a chance to gain revenge for last season's FA Cup final defeat against Liverpool as the two Premiership heavyweights have been drawn against each other in round four.
The Gunners will have home advantage in what is the biggest tie of the round to be played on the last weekend of this month.
However, there is also the possibility of a cup meeting between Middlesbrough boss Steve McClaren and Sir Alex Ferguson, his mentor at Manchester United before McClaren left Old Trafford in the summer.
However, Middlesbrough must first get through a tricky third-round tie at First Division Wimbledon which was postponed this weekend because of a frozen pitch.
Cardiff, the Second Division conquerors of Premiership leaders Leeds, face a trip to either Southend or Tranmere while Bristol Rovers, who put out another top-flight side in Derby, travel to Gillingham.
And there is the chance of a north-east derby between Newcastle, fourth in the Premier League, and Darlington at Feethams if the Third Division club can overcome the challenge of Peterborough in their rearranged third-round tie. -PA