Nottingham Forest's reward for beating Charlton in the FA Cup is a fourth round tie against Chelsea.
The League One side will visit the Premiership champions in one of the more enticing games, while Arsenal will entertain Bolton.
Manchester United will host Portsmouth and Watford will visit West Ham in other all-Premiership encounters.
Giantkillers Swansea knocked out Sheffield United and will visit Championship side Ipswich Town.
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Blackburn face a tricky tie as they will travel to Luton, who were runners-up in 1959.
Luton boss Mike Newell will have extra motivation to lead his side to victory as he enjoyed a spell at Ewood Park.
Bristol Rovers boss Paul Trollope will try to instigate an upset against his former club Derby when he takes his League Two side to play the Championship high-flyers at Pride Park.
Premiership strugglers Middlesbrough already face a difficult third round replay at Hull and face the prospect of a visit to either Bristol City or Coventry if the negotiate their way into the next round.
The thought of playing Chelsea is a mouth-watering prospect
Forest boss Colin Calderwood
Speaking about the Nottingham Forest tie, Reds manager Colin Calderwood said the prospect of playing the champions was "mouth-watering".
"I know I said on Saturday after the game that I wanted Tottenham but after that I was looking for Chelsea, Manchester United or Arsenal," he told Forest's website.
"It's a fantastic draw for us. The fact that it's an away draw and we're going to Stamford Bridge really whets the appetite because it's a chance for us to enjoy a touch of glamour.
"I don't mind admitting I cheered when I heard the draw, and there's no denying the thought of playing Chelsea is a mouth-watering prospect."
Arsenal v Bolton
West Ham v Watford
Bristol City v Middlesbrough
Chelsea v Nottingham Forest
Ipswich Town v Swansea
Tottenham v Southend Utd
Barnet v Plymouth Argyle
Birmingham City v Reading
Derby County v Bristol Rovers
Manchester City v Southampton
Crystal Palace v Preston North End
Manchester United v Portsmouth
Blackpool v Norwich City
Luton Town v Blackburn Rovers
Wolves v WBA
Fulham v Stoke City
The ties will be played on Friday 26, Saturday 27 and Sunday 28 January.