Liverpool has been drawn at home to Merseyside rival Everton in the FA Cup third round, while holder Manchester City will start the defence of its title at home to third-tier Port Vale.
The Toffees face Jurgen Klopp's side on Wednesday in the Premier League and will make the short trip to Anfield for a second time this season during the first week of January.
Pep Guardiola's City thumped Watford 6-0 in last season's final and has been given a favourable draw to kick-start its 2019-20 campaign, with John Askey's League Two side pitching up at the Etihad Stadium.
Manchester United faces a difficult away tie against Premier League rival Wolves, which knocked them out of the competition last season's quarterfinals, while Arsenal welcomes Championship leader Leeds United to the Emirates Stadium.
New Tottenham boss Jose Mourinho takes his side to Middlesbrough, managed by former Spurs defender Jonathan Woodgate, and Chelsea hosts Nottingham Forest. Ties will take place between January 3 and 6.
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