Liverpool will host Everton in the third round of the FA Cup, while Championship leaders Leeds United will travel to Arsenal.
Holders Manchester City will welcome League Two side Port Vale and Manchester United go to Wolves in a repeat of last season's quarter-final.
National League side AFC Fylde, the lowest ranked team definitely through to the third round, will travel to Premier League Sheffield United.
Ties are played between 3-6 January.
Boston, of the sixth-tier National League North, will host Premier League opposition in Newcastle United, if they can come through a replay against Rochdale on Tuesday, 10 December.
Fellow non-league sides Hartlepool and Eastleigh also face replays, but could meet Oxford United and Barnsley respectively should they progress.
Merseyside rivals Liverpool and Everton meet on Wednesday night in the Premier League, with both sides in wildly differing form.
Jurgen Klopp's Reds are eight points clear at the top of the league, while Everton sit two points above the relegation zone with pressure mounting on boss Marco Silva.
All three of the most recent meetings between Leeds and Arsenal have come in the third round of the FA Cup, the Gunners winning 1-0 in 2012 and also prevailing 3-1 in a replay in January 2011, following a 1-1 draw.
Wolves reached their first FA Cup semi-final in 21 years by beating Manchester United in last season's quarters, while Manchester City will be wary of falling victim to lower-league Port Vale after going out to then-League One side Wigan in the fifth round in 2018.
Draw in full
Leicester City v Wigan Athletic QPR v Swansea City Fulham v Aston Villa Chelsea v Nottingham Forest Wolves v Manchester United Charlton Athletic v West Brom Rochdale or Boston United v Newcastle United Cardiff City v Forest Green Rovers or Carlisle United Oxford United v Exeter City or Hartlepool United Sheffield United v AFC Fylde Southampton v Huddersfield Town Liverpool v Everton Bristol City v Shrewsbury Town Bournemouth v Luton Town Brighton v Sheffield Wednesday Bristol Rovers or Plymouth Argyle v Coventry City or Ipswich Town Eastleigh or Crewe Alexandra v Barnsley Manchester City v Port Vale Middlesbrough v Tottenham Reading v Blackpool Watford v Tranmere Rovers Preston v Norwich City Millwall v Newport County Crystal Palace v Derby County Solihull Moors or Rotherham United v Hull City Brentford v Stoke City Fleetwood Town v Portsmouth Arsenal v Leeds United Gillingham v West Ham United Burton Albion v Northampton Town Burnley v Peterborough United Birmingham City v Blackburn RoversDISCLAIMER: The Views, Comments, Opinions, Contributions and Statements made by Readers and Contributors on this platform do not necessarily represent the views or policy of Multimedia Group Limited.
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