The date was Tuesday, November 4, 2014.
Liverpool players skulked off the Bernabeu pitch, having succumbed by a solitary goal to the far superior Real Madrid, despite the super-human efforts of a past his best Kolo Toure.
Some have suggested that it signalled the beginning of the end for Brendan Rodgers, who, just months after nearly landing the holy grail of a 21st century title for the Redmen, sent a second string XI out for a crunch Champions League game.
The thinking by the Ulsterman was presumably to rest the legs of Philippe Coutinho, Steven Gerrard and Raheem Sterling for a league game against Chelsea days later.
Sitting 7th in the table going into the game, Rodgers concluded that accepting a likely loss in Madrid would aid his side in edging out Jose Mourinho's men.
They would lose 2-1 at Anfield.
Things would get worse before they got better for the Reds, who never recovered under Rodgers.
Having lost Luis Suarez to Barcelona and Daniel Sturridge to the treatment table, a drop-off in the league was expected. However, back in the Champions League for the first time this decade, Rodgers' Reds were doing themselves a serious disservice.
Having only taken three points from their first four games, things didn't improve with a dour draw away in Bulgaria to Ludogorets.
Setting up a final day play-off with Basel, Liverpool had to win. Things didn't go to plan, a late Steven Gerrard free-kick only enough for a 1-1 draw. Liverpool were out.
Gone was the free flowing attacking football that had captured hearts and minds months earlier.
Gone was the never say die attitude that had seen the Reds come so close to the title they craved.
Gone was a chance of a Champions League run in the face of a disappointing league campaign.
Gone, less than a year later, was Rodgers.
Can Klopp win Liverpool number six?
Jürgen Klopp, Rodgers' replacement and still Liverpool manager today, showed pedigree on the European stage in his first season.
With the Reds getting through their Europa League group, an assault on the competition as the only way of getting into the following season's Champions League.
Champions League calibre teams were beaten in the knockout stages, with Manchester United, Borussia Dortmund and Villarreal brushed aside before ultimately falling to Sevilla at the final hurdle.
Liverpool, of course, have the opportunity to avenge that defeat in Switzerland after they were drawn against Sevilla in the group stage.
Spartak Moscow and Maribor make up the rest of a group that Liverpool are expected to sail through with ease. Then again, they were expected to qualify in 2014.
The difference now is that the Reds can cope without Luis Suarez. Only Philippe Coutinho remains a consistent starter from that attack of Rodgers' final season.
Mohamed Salah, Roberto Firmino and Sadio Mane make up a deadly front three that helped knock six past Bundesliga side Hoffenheim in two games during the play-off.
An appetite for proper European football was further wet in pre-season with Bayern Munich swept aside and, if Liverpool can this time make it through the group stage, fans may start to dream of once again being a European force.