It has only been three years since the Reds last sampled Champions League football, yet it feels like an eternity for a club which has seen so much change since Brendan Rodgers last guided them there.
On the back of a second-place finish that promised the dawn of a a new era, Luis Suarez was sold, over £100m was spent and Rodgers lasted just over a year.
It was Liverpool’s first venture into the Champions League in five years, and much was expected of a young side who had come so close to a shock league title win.
But the upheaval that arrived in the summer of 2014 rocked a tight-knit side that had been on an upward curve.
Nine players were brought in for a total of £117m, Mario Balotelli the most eye-catching of them all, but they failed to fill the considerable Suarez-shaped hole.
Injury to Daniel Sturridge blunted Liverpool’s attack ever further, and the England striker was unable to play a single minute of Liverpool’s Champions League campaign that season – a wait that still goes on.
The group stage began with an unconvincing 2-1 home win over Bulgarian minnows Ludogorets, with Steven Gerrard’s stoppage-time penalty sparing their blushes.
There followed defeat in Switzerland, to Basle, which accompanied a slide down the Premier League table.
Liverpool’s teething problems were then laid bare by Real Madrid, the reigning European champions, who thrashed them 3-0 at Anfield thanks to three first-half goals.
Despite the illustrious opposition, and the prize on offer, the atmosphere at Anfield was oddly tepid that night, with former Manchester United man Cristiano Ronaldo handed a generous round-of-applause as he was substituted 15 minutes from time.
It seemed apt for a European campaign that never got going. What followed was perhaps the beginning of the end for Rodgers.
A trip to the Bernabeu with nothing to lose but everything to gain turned into a damage limitation exercise. Rodgers left Gerrard, Philippe Coutinho, Jordan Henderson and Raheem Sterling on the bench.
Fabio Borini played up front and Kolo Toure in defence. Liverpool lost 1-0.
A last-minute equaliser conceded on the return trip to Bulgaria cost Liverpool all three points against Ludogorets, despite the collector’s item of a goal from Rickie Lambert.
It left the Reds needing a win at home against Basle to creep their way into the last 16.
An improvement in league form had seen Liverpool go three games without defeat, though it had been brought about by a conservative style of play totally anathema to Rodgers.
For the do-or-die finale, Lambert began up front on his own, Jose Enrique was at left-back, and Coutinho benched.
Liverpool fell behind after 25 minutes, saw substitute Lazar Markovic sent off in the second half before Gerrard fired home a free-kick nine minutes from time.
It was all they could muster, and they exited with a whimper in front of their own supporters, demoted to the Europa League.
If there is anything Jurgen Klopp can learn from that botched campaign as he kick-starts Liverpool’s return against Sevilla on Wednesday night, it is to back his players and his own methods.
Rodgers found himself caught between two stools, unwilling to attack with the verve that had been his side’s blueprint, and unable to tighten a creaky defence.
Liverpool deservedly exited at the group stage in 2014 full of regret and with a tinge of embarrassment. Klopp will not allow that to happen.
He has already guided the club to a Europa League final and overseen one of the great European nights at Anfield. He will stick to his guns and go full throttle in an attempt to restore the club to their place in the European elite.