Elsewhere in the draw Blue Square Premier League side Barrow have been handed a trip to Premier League side Middlesbrough in the third round after shocking Brentford on Friday.
Meanwhile Histon, conquerors of former winners Leeds this afternoon will be at home once more after being drawn against Swansea City while Forest Green Rovers will entertain another Championship side in Derby County.
Fellow non-league side Kidderminster Harriers make the short trip to Coventry City while Eastwood Town may have a local derby to look forward to in the cup after being drawn with Notts County or Kettering.
Winners of the 2008 FA Cup Portsmouth will play Bristol City at Fratton Park while Premier League Champions Manchester United travel to Southampton and Chelsea entertain Southend United. Arsenal meanwhile face a clash with Championshp side Plymouth.
Ties will be played on the weekend of 3rd/4th January 2009.
The full draw is:
Portsmouth v Bristol City
Sheffield Wednesday v Fulham
Preston v Liverpool
Birmingham v Wolves
West Ham v Barnsley
Middlesbrough v Barrow
Hull City v Newcastle United
Hartlepool United v Stoke City
Chelsea v Southend United
Manchester City v Nottingham Forest
Cardiff City v Reading
Ipswich Townv Chesterfield/Droylsden
Charlton Athletic v Norwich City
WBA v Peterborough/Tranmere
Torquay United v Blackpool
Leyton Orient v Sheffield United
Southampton v Manchester United
Millwall v Carlisle/Crewe
Histon v Swansea City
Forest Green v Derby County
QPR v Burnley
Leicester City v Crystal Palace
Tottenham v Wigan Athletic
Morecambe/Cheltenham v Doncaster
Arsenal v Plymouth Argyle
Notts County/Kettering v Eastwood Town
Bournemouth/Blyth v Blackburn
Macclesfield v Everton
Watford v Scunthorpe
Sunderland v Bolton Wanderers
Coventry City v Kidderminster
Gillingham/Stockport v Aston Villa