In the only all Premiership clash Boro have a chance of revenge against Blackburn who knocked Boro out of the Worthington Cup earlier in the season.
The tie of the round is undoubtedly Kevin Keegan's return to Newcastle, with his Man. City side who beat Ipswich 4-1 this afternoon.
The full draw is as follows:
Tottenham/Bolton v Tranmere
Newcastle v Man City
Arsenal v Gillingham/Bristol R
Chelsea/West Ham v Preston
Boro v Blackburn
Everton v Crewe
Walsall v Fulham
West Brom v Cheltenham
The matches will be played over the weekend of 16th and 17th of February.