Holders Liverpool have been drawn at home to 2005 winners Arsenal in the third round of the FA Cup.
The 2004 Cup winners Manchester United were also handed a tough home tie against Martin O'Neill's Aston Villa.
Paul Ince's Macclesfield will travel to Chelsea, while Portsmouth face Wigan and Everton meet Blackburn Rovers in all-Premiership ties
Tamworth are at home to Norwich, while Nottingham Forest will meet Charlton after beating Salisbury on a replay.
Also decided on a replay was Bolton's opponents, with Doncaster winning through to the match against the Premiership side after they beat Mansfield.
But it is Arsenal and Liverpool that will meet at Anfield in the round's biggest draw, five years after the two clubs met in the final of the competition in 2001.
Michael Owen scored two late goals in that match as the Reds won the trophy 2-1.
Arsenal got some revenge by knocking Liverpool out the following season in the fourth round.
The two sides also met at the semi-final stage in 1980, with three replays needed before Arsenal won through to the final, and the 1971 final which the Gunners won in extra-time.
Full draw:
Blackpool v Aldershot
Barnet v Colchester
Sheff Utd v Swansea
Reading v Burnley
Portsmouth v Wigan
Doncaster v Bolton
West Ham v Brighton
Leicester v Fulham
Derby v Wrexham
Wolves v Oldham
Chester v Ipswich
Man Utd v Aston Villa
Sheff Wed v Man City
Tamworth v Norwich
Nottm For v Charlton
Cardiff v Tottenham
Preston v Sunderland
Liverpool v Arsenal
Bristol Rovers v Hereford
Watford v Stockport
Crystal Palace v Swindon
Bristol City v Coventry
Peterborough v Plymouth
QPR v Luton
Southend v Barnsley
West Brom v Leeds
Hull v Middlesbrough
Birmingham v Newcastle
Torquay v Southampton
Everton v Blackburn
Chelsea v Macclesfield
Stoke v Millwall
Ties will be played on the 6 and 7 of January.