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 Rovers