In their pomp, Liverpool won League Cups for fun but after suffering their worst start to a league campaign in 101 years, Wednesday's third round clash at West Bromwich Albion takes on extra significance.
Should Liverpool lose, it would add to the pressure already building on new manager Brendan Rodgers after defeat by Manchester United left his team third from bottom in the Premier League and casting envious glances at high-flying neighbours Everton.
Sunday's 2-1 loss was Liverpool's third defeat in their opening five games, with draws against Manchester City and Sunderland providing them with their only points of the fledgling campaign.
It would be wrong, however, to suggest that an autumnal gloom was encircling the club in the way it did when former boss Roy Hodgson suffered a similarly inglorious start to his short-lived Liverpool reign in the 2010/11 campaign.
That period coincided with a bitter ownership struggle and the threat of administration and perhaps annihilation hanging over the club.
Now, Liverpool fans who fought to get rid of previous owners Tom Hicks and George Gillett and booed Hodgson's every defeat are able to see green shoots of recovery in Rodgers' new-look side.
Despite scoring only four times in the league, Rodgers' Liverpool have been pleasing on the eye.
The Northern Irishman, who arrived from Swansea in June, describes his philosophy as "death by football" and his commitment to the relentless retention of possession fits in neatly with the long-held traditions of the club.
While style over substance counts for little as far as the cold currency of Premier League points is concerned, the manner of Liverpool's defeat by bitter rivals United gave cause for optimism to their suffering fans.
"If we keep playing like that and showing that amount of effort and determination, then it will only be a matter of time [before we get our first win]," captain Steven Gerrard told Sky Sports.
"If you analyse all of our performances, it's not that we haven't been playing well enough - maybe we just need a bit of luck. We'll keep plugging away and it will come eventually."
When teams are in trouble they traditionally revert to tried and trusted formulae with experienced professionals being handed the burden of responsibility for dragging sides out of the doldrums.
Given the context of their current situation, therefore, Rodgers' decision to blood young players should be applauded and suggests the club are prepared to endure some short-term pain for long-term gain.
For a traditionally ferocious encounter, five of Liverpool's starting XI on Sunday were under 23 and when 21-year-old Fabio Borini was forced off at half-time, Rodgers made a brave decision to throw 18-year-old Spaniard Suso into the Anfield cauldron.
The teenager did not disappoint and was involved in the creation of Liverpool's only goal and along with 17-year-old Raheem Sterling, who tormented Patrice Evra with his pace, was a bright spot on an otherwise difficult day.
"Fabio goes off and young Suso came on and I think you could see the excitement," said Rodgers.
"There are a group of young players here who hopefully in the next few years can take the club forward."
Rodgers' commitment to youth development would suggest he has been given the backing of the club's owners to build for the future, but patience at boardroom level is a quality that extends only so far.
The Fenway Sports Group, who took control of the club in October 2010, have already sacked two managers.
But unlike Hodgson, who they inherited and Kenny Dalglish, who was axed in May, they say Rodgers fits the blueprint of the young and hungry technocrat they had always wanted to install in the hotseat.
The owners themselves have not been immune from criticism and came under fire at the end of the transfer window for failing to complete the signing of 29-year-old forward Clint Dempsey while sanctioning Andy Carroll's loan departure to West Ham United.
Should Liverpool's current struggles in front of goal continue, Rodgers could legitimately hold this as mitigation.
He might also plead for patience given Liverpool have already played last season's top three in his opening five league matches while trying implement his vision for the club.
Their plight is perhaps all the more painful for fans given the form of local rivals Everton, who are third and playing with swashbuckling panache.
If Liverpool's owners start to question their commitment to Rodgers' vision they would do well to remember that Everton have stuck by manager David Moyes through thick and thin over the last 10 years and their perseverance has paid dividends.
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