After a Barclays Premier League defeat to Manchester United in their previous fixture, Liverpool lost a glorious opportunity to steal a march on their rivals in the race for the top-four.
In a game that many described as a 'six-pointer' - it was a hard result for many Kopites to swallow as it pushed the promise of a return to the Champions League back even further.
With Liverpool now sitting in ninth place, any talk of a title challenge has been effectively wiped out and with just 16 games remaining the task at hand for Jürgen Klopp to even steer his side into the top-four has become much more diifcult.
With an FA Cup clash with Exeter City facing the Reds on Wednesday as well as a League Cup decider against Stoke City six days later, the surrounding cup competitions are creating a claustrophic atmosphere around the club with games coming thick and fast.
Top four challenge - out of the window?
Swapping managers mid-way through a season is always a difficult challenge. Brendan Rodgers left Liverpool with his side sitting 10th in the Premier League, Klopp has improved this standing by one position but after coming so close two seasons earlier anything other than a top-four finish will be seen as a disappointing finish.
The Liverpool side that Klopp has inherited has had very little adding to by the German, who has only made one loan signing and a long-term addition who has gone out on loan for the remainder of the current campaign.
Add to that the fact he has had very little time to work with his full squad since their first fixture against a strong Tottenham Hotspur, and it has been made even more difficult for his side. However, with Liverpool still battling in three other cup competitions is it possible the Reds boss took his eye off the league?
With Liverpool now extreme outsiders to make it into the top-four, should Klopp be looking at the cups as a more direct route into European competition next season? In his first season at Borussia Dortmund, the German won the T-Home Supercup while finishing sixth in what could now mimic his first season in English football.
With 16 games left to play the Reds would need to pick up close to maximum points in order to sustain a realistic challenge for the top-four as the top 12 teams arguably possess the ablity to try and work their way into Europe. If you want to be in with a chance at a top-four finish, the typical guideline points total is around 70 and with Liverpool currently on 31 they would need to pick up 39 points which translates to 13 wins from their remaining 16 games.
This could be a possibilty for a club solely focussed on the league which Rodgers said was a huge factor in Liverpool finishing so high in the 2013/14 season, but with them also challenging for other trophies coupled with a thin squad - the 'realistic' target of a top-four finish has been shattered with the Reds most likely to have to settle for a place in the Europa League.
With established and stable sides like Manchester United and Tottenham Hotspur some way ahead of them in the table, it is unlikely that the Reds will be able to catch up.
Instead, a sixth place finish could be seen as a success given that Klopp only took over in October, but a more lasting challenge next season should be seen if he works well in the transfer market and avoids any more injury crises.
Domestic cup competitions - success possible?
Liverpool have been without a trophy since winning the Carling Cup in 2012 with Kenny Dalglish at the helm. Four years without a major trophy is a lifetime for a club of this stature and the Reds have a glorious opportunity of bringing the now named Capital One Cup back to Anfield.
With Stoke City making their way to L4 on January 26, Liverpool should feel fairly confident about their chances of advancing into the final of the trophy as they carry a one-nil advantage from the previous meeting and have already beaten Stoke twice this season, with the first win coming on the opening day of the Premier League.
The realistic prospect of a trophy does not solely represent silverware, it offers the winner the chance of playing in the Europa League the following season, with the eight-time winners just two wins away from a ninth triumph it could cap off a difficult end to Klopp's first season in charge.
The FA Cup is the second domestic competition Liverpol are involved in, and if anything the tournament has only added to the looming crisis for the club as drawing to Exeter in the third round offered Liverpool a further match to contest, coming at a time when Klopp's side are riddled with injuries.
Klopp set out a weakened side for the first tie with young players like Cameron Brannagan and Brad Smith presented with the rare opportunity to showcase their talents and the manager is set to repeat his tactics in the replay. He might feel risking his bigger players - henceforth risking more injuries - could be catastrophic to the season as he is already without big names such as Phillipe Coutinho, Martin Skrtel and Dejan Lovren.
It is feasible that the fixtures in the FA Cup will see fringe team players get a run about while first-team stars are rested. It works well for both sides and would allow Klopp, as well as the regular XI, the chance to focus on more important forthcoming fixtures.
The Reds have a strong chance of winning the Capital One trophy this year above anything else, and if that is accomplished, the league decision is less decisive looking towards the following season.
An FA Cup challenge alongside this seems a step too far and using that as a kind of test to the younger crop of players will be most beneficial, though it more than probably surrenders a real shot at making it to Wembley in this competition.
Europa League - a step too far?
Liverpool are currently in the last 32 of the Europa League with their opponents FC Augsburg presenting tricky, but beatable, opposition in a season already filled with obstacles.
The Reds travel to Germany to face the Bundesliga outfit in February and are urrently one of the favourites to take home the trophy alongside other big sides such as Manchester United, Napoli and Borussia Dortmund. Indeed, just five matches stand between the team lifting the silverware in the final at St. Jakob Park in Basel.
Liverpool last won the Europa league in 2001 when it was named the UEFA Cup, beating Spanish side Alaves 5-4 in golden goal. Klopp has never got his hands on a European trophy and after coming so close in 2013, he will want to do everything he can to win this one - particularly with success in Europe so highly-regarded on Merseyside.
It is likely that with the squad already lacking major players and firepower in the league, facing stronger and stronger sides as the competition wears on will take its toll but winning the Europa League does give the winner an opening into the Champions League next year, making it a hugely desirable trophy.
Liverpool should expect to beat Augsburg and progress as far as the quarter, and possibly even semi, finals at the very minimum, but with other trophies nearing their end, this competition will more than likely take a back seat role in terms of importance.