The Reds resume the 2022-23 campaign by facing their fellow Premier League side at Etihad Stadium with a berth in the Carabao Cup quarter-finals up for grabs.
Here, we take a look back at past contests between the teams in the competition…
1969-70 (third round) – City 3-2 Liverpool
City got the better of the first League Cup meeting back in September 1969.
The hosts raced into an early lead at Maine Road that was soon levelled in fortuitous circumstances as an attempted clearance struck Liverpool’s Alun Evans and spooled into the net.
But the Reds’ luck was seemingly used up in that incident as, having fallen two goals behind and halved the deficit through Bobby Graham, a late spell of pressure did not yield the second equaliser required.
1980-81 (semi-finals) – Liverpool 2-1 (agg) City
There was a similar pattern but different outcome when Liverpool, now under the charge of Bob Paisley, returned to Maine Road for the first leg of a semi-final.
City again tested their visitors for much of the encounter but this time the Reds held firm and took control of the two-legged tie courtesy of Ray Kennedy’s strike late on.
That grip was tightened when Kenny Dalglish opened the scoring 23 minutes into the return clash at Anfield, though nerves were increasingly frayed as their opponents levelled soon after the interval and proceeded to fashion a series of chances.
Paisley’s boys saw it out, however, and would go on to win the trophy for the first time in the club’s history – and begin a run of four consecutive triumphs – later in the season.
1995-96 (third round) – Liverpool 4-0 City
Roy Evans’ Reds maintained their defence of the cup they had won in the previous campaign with an ultimately comfortable home victory.
John Scales put Liverpool in front with just nine minutes on the clock, though they laboured to add to the scoreline and end the tie for sure.
Qualification was sealed in the closing stages, however, as Robbie Fowler, Ian Rush and Steve Harkness netted in rapid succession.
2011-12 (semi-finals) – Liverpool 3-2 (agg) City
Liverpool’s second-most recent triumph in the League Cup, back in 2011-12, was partly made possible by a thrilling two-legged semi-final defeat of City.
With Dalglish in the dugout, and in an echo of their previous semi-final fixture three decades earlier, the Reds won the away leg 1-0, Steven Gerrard dispatching a penalty to win it.
A scintillating and dramatic conclusion ensued in the second meeting at Anfield, where the away outfit twice took the lead either side of another Gerrard spot-kick.
But the final word went to former City man Craig Bellamy, who finished off a slick attack in front of the Kop to make it 2-2 and send Liverpool back to Wembley.
2015-16 (final) – City 1-1 (3-1 pens) Liverpool
It was the tournament’s deciding match when the sides last met in League Cup action, in 2016.
Jürgen Klopp’s first final as Reds manager was an absorbing showdown in which Philippe Coutinho fired home in the closing stages to equalise an effort from Fernandinho early in the second half.
Extra-time could not separate them at Wembley and penalties eventually had to, with Manuel Pellegrini’s City prevailing 3-1 in the shootout from 12 yards to secure the silverware.