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Gillingham have been drawn away to Premier League Wolves in the Carabao Cup Fourth Round.
Gills were the lowest-ranked side left in the hat and they didn't manage to avoid one of the 10 Premier League clubs left in the competition.
Neil Harris' men have already knocked out Brentford in the Third Round on penalties after a 1-1 draw in west London on Tuesday.
A win against Wolves would see Gillingham reach the Fifth Round for the first time in their history.
Gills reached the Fourth Round of the League Cup in 1963/64 when they lost 4-1 at Leicester, as well as the 1996/97 season when they were knocked out 1-0 at Ipswich.
Wolves recently appointed former Spain and Real Madrid boss Julen Lopetegui as their new manager. They sit 19th in the Premier League, only above Nottingham Forest on goal difference, with 10 points in 14 games and just two league wins to their name.
They needed an 85th-minute goal from Boubacar Traore to defeat Leeds 1-0 in the previous round.
Elsewhere, the tie of the round was Manchester City being paired at home to holders Liverpool.
Ties are due to be played on Wednesday, December 21 and Thursday, December 22.
Carabao Cup Fourth Round draw:
Wolverhampton Wanderers v Gillingham
Southampton v Lincoln City
Blackburn Rovers v Nottingham Forest
Newcastle United v AFC Bournemouth
Manchester City v Liverpool
Manchester United v Burnley
Milton Keynes Dons v Leicester City
Charlton Athletic v Brighton & Hove Albion