Liverpool crashed out of the last 32 of the Europa League with a penalty defeat to Besiktas after the pair could not be separated after 210 minutes of football.
The Reds went into the game in Istanbul with a slender 1-0 lead after winning at Anfield a week earlier in the first-leg thanks to a Mario Balotelli penalty.
However, it was the Turkish side who broke the deadlock when Toglay Arslan fired his 20-yard effort into the top corner mid-way through the second-half leaving Simon Mignolet helpless.
Demba Ba almost sealed the game for Besiktas but his effort from close-range crashed against the bar and the match went into injury time.
Neither side created much in the 30 minutes and the game then went to penalties. At 5-4, Dejan Lovren took Liverpool's final penalty but smashed hit effort over the bar to send Besiktas into the last 16 of the competition.
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In a game that leaves Brendan Rodges' men in just one cup competition, there were several things we learned.
Sturridge is still not at his best
Daniel Sturridge netted 21 Premier League goals last season however has struggled to find the target this term since coming back from his five-month injury.
It may be a physiological effect on the England international, too scared to once again become side-lined, but he has been well below-par in recent weeks.
Sturridge had two decent chances in the first-half, however fluffed his lines on both occasions. When played in by Balotelli, the former Chelsea man had the oppurtunity to strike it first time on his right-foot but instead messed around with the ball and wasted the opening.
It was not just the chances that Sturridge wasted either that but used the ball poorly at times.
His passing was a bit rushed, almost like he did not want the ball at his feet and delegated responsibility elsewhere when in decent positions.
After such a long injury, Sturridge was never going to be the player he was last season. Of course, it will take time however it has to been sooner rather than later. He managed 105 minutes on the pitch and hopefully that game-time will help him regain his spark.
Quite often this season, Alberto Moreno has went about his game confidently and quietly on the left-wing.
He hasn't caused any headlines, he hasn't been awarded man of the match, but he has been consistent.
Against Besiktas, the Spaniard stepped up a level and was Liverpool's best player on the pitch.
From the first whistle, Moreno was confident when driving forward with the ball and the majority of the Reds' chances came directly through him.
After the break, it was the home side who began getting the upper hand and it forced the former Sevilla man to terminate his attacking credentials and instead stick to his defensive duties.
Moreno was solid for the most part winning tackles and headers and was as strong as an ox knocking Besiktas men off the ball.
Lovren must improve
It was Dejan Lovren who knocked Liverpool out of the Europa League.
However, it was not for his penalty miss.
Re-watching Besiktas' goal, Lovren got caught ball watching. He was dragged towards the play instead of identifying where Arslan was and, although it was a top finish, the shot should have never had a chance to head towards goal.
It was not the first time that the Croat was caught out during the game and in recent weeks.
Earlier in the second-half, Arslan fired a shot from 35-yards out that just flew past Mignolet's left-post. From the distance he was, the Besiktas midfielder should never have even had the chance to even contemplate shooting. It was Lovren marking him and once again the ex-Southampton centre-back gave the German too much space.
£20 million was the fee paid for Lovren in the summer and it is indeed looking like an incredibly poor piece of business.
With Kolo Toure proving his worth once again when making his first start since returning for the African Cup of Nations, it seems that Lovren will now go to the end of the pecking order.
The worst possible outcome
Rodgers has stated how badly he wants a trophy at the end of this campaign, however has to admitted he would also like a top-four finish in the Premier League.
It was always going to be difficult for the Liverpool boss to juggle the two competitions, especially with the FA Cup also a piece of silverware for the taking.
After a gruelling 120 minutes on the massive pitch of the Ataturk, the Reds now have little under two days to prepare for Manchester City on Sunday.
If Liverpool were still in the Europa League then it would not be as bad however Rodgers has been left in the worst circumstance possible.
Last Sunday, all three teams who had competed in the Europa League performed under-par; Everton were awful in their 2-2 draw with bottom of the table Leicester City, Tottenham Hotspur were lucky to scrape a 2-2 draw with West Ham United and Liverpool did not perform all that well despite beating Southampton 2-0.
In contrast to the Merseyside club, Manchester City have four days to get themselves ready for their trip to Anfield after Tuesday's 2-1 defeat to Barcelona.
Rogers' men are just two points off fourth-place and a victory against the Citizens would give the Reds' confidence a major boost.
However, preparations have gone poorly and instead Liverpool could slip down the greasy pole of a top-four finish.
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