Liverpool will face Wolverhampton Wanderers in the FA Cup third round after the draw took place on Monday evening.
Jurgen Klopp's side are set to travel to the Molineux on either Sunday, January 6 or Monday, January 7.
Liverpool will be looking to fare better in the FA Cup, after crashing out in the League Cup to Maurizio Sarri's Chelsea earlier this season.
Liverpool have exited the FA Cup in the fourth round in all off Jurgen Klopp's full seasons in charge.
The Reds lost 3-2 to West Bromwich Albion last year following a 2-1 victory over Everton on Virgil van Dijk's debut in the third round.
During Klopp's first full term in 2016-17, the Reds also crashed out to Wolves with a 2-1 loss at Anfield against a then-Championship side.
Liverpool 1-2 Wolverhampton Wanderers: Jurgen Klopp's side in shock FA Cup exit
Nuno Espírito Santo's Wolves side are highly rated with the likes of Raul Jimenez, Ruben Neves and Joao Moutinho all impressing. The Midlands club sit in twelfth place in the Premier League so far.
Liverpool will have a taste of what's to come as they face Wolves away from home on December 21, amidst a busy festive period for Klopp's side.
FA Cup 3rd round draw
Accrington vs Ipswich
Aston Villa vs Swansea
Bolton vs Walsall/Sunderland
Bournemouth vs Brighton
Brentford vs Oxford
Bristol City vs Huddersfield
Burnley vs Barnsley
Chelsea vs Nottm Forest
Crystal Palace vs Grimsby
Derby vs Southampton
Everton vs Lincoln
Fulham vs Oldham
Gillingham vs Cardiff
Guiseley/Fleetwood vs AFC Wimbledon
Manchester City vs Rotherham
Manchester United vs Reading
Middlesbrough vs Peterborough/Bradford
Millwall vs Hull
Newcastle vs Blackburn
Norwich vs Portsmouth
Preston vs Doncaster
QPR vs Leeds
Sheffield Utd vs Barnet
Sheffield Wed vs Luton
Shrewsbury vs Stoke
Solihull/Blackpool vs Arsenal
Tranmere/Southport vs Tottenham
West Bromwich Albion vs Wigan
West Ham United vs Birmingham
Woking vs Watford
Wolves vs Liverpool
Wrexham/Newport vs Leicester City
Ties to be played January 4-7.