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
Arsenal and Liverpool will meet at Anfield in the round's biggest draw.
The two clubs met in the final of the competition in 2001, with Michael Owen scoring two late goals in a 2-1 Liverpool win.
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.
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Full draw: Blackpool v Aldershot/Basingstoke
Barnet v Colchester
Sheff Utd v Swansea
Reading v Burnley
Portsmouth v Wigan
Mansfield/Doncaster v Bolton
West Ham v Brighton
Leicester v Fulham
Derby v Wrexham
Wolves v Oldham
Bury/Chester v Ipswich
Man Utd v Aston Villa
Sheff Wed v Man City
Tamworth v Norwich
Salisbury/Nottm For v Charlton
Cardiff v Tottenham
Preston v Sunderland
Liverpool v Arsenal
Bristol Rovers/Bournemouth 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/Leyton Orient v Southampton
Everton v Blackburn
Chelsea v Macclesfield
Stoke v Bradford/Millwall
Ties will be played on the 6 and 7 of January.
