Blue Square Premier League side Barrow have been handed a trip to Premier League side Middlesbrough as reward for shocking Brentford on Friday.
Histon, conquerors of former winners Leeds United on Sunday, will be at home again in the third round, after being drawn against Swansea City while Forest Green Rovers will entertain another Championship team - Derby County.
Kidderminster Harriers make the short trip to Coventry City, while Eastwood Town could have a local derby to look forward to after being paired with Notts County or Kettering.
Everton have a tough test to look forward to after being pitted with Macclesfield Town.
The full draw: 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 Town v 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.
