Liverpool crashed out of the last 32 of the Europa League, losing to Besiktas 5-4 on penalties at the Ataturk Stadium.
Dejan Lovren missed the decisive kick in the shoot-out, after Tolgay Aslun had levelled the tie with a superb curling shot on 72 minutes.
Mario Balotelli was given his first start since November 8 alongside Daniel Sturridge in attack, whilst Emre Can was moved forward into midfield to accomodate Kolo Toure in a new look back three.
The Reds impressed during a first half in which the home crowd looked to make the atmosphere as hostile as possible.
After a 20 minutes in which Liverpool tried to silence the crowd by holding onto the ball, Brendan Rodgers men began to create opportunities.
Daniel Sturridge was wasteful when set through by Mario Balotelli, taking too many touches before eventually forcing goalkeeper Cenk Gonen into a smart save from a right footed shot.
Raheem Sterling also threatened to break through behind on a couple of occasions, first failing to pick out a teammate with a pass when well placed, before forcing Gonen into a routine save with a shot from the edge of the box.
The 20-year-old then saw another effort deflected wide as the Reds tried to make their superiority tell. Failure to score in that period proved costly for the Reds as they began to drop deeper early in the second half.
Besiktas – urged on by their passionate supporters – began to pile pressure on the Liverpool goal, with Simon Mignolet forced into a couple of routine saves from long range.
The Reds could simply not keep a hold of the ball however, and produced next to nothing in the attacking third.
They were made to pay for this on 72 minutes, when substitute Arslan curled a superb shot past Simon Mignolet from the egde of the box, following a clever flick from Demba Ba.
The former Chelsea forward almost won it with just a minute to play, firing a shot against the under-side of the bar from close range after the ball had broken kindly off Martin Skrtel from a corner.
That miss ensured there would be another 30 minutes of extra time – hardly ideal when you consider the Reds face Manchester City in Sunday’s early kick off.
Extra time played out much as the second half had, with Besiktas enjoying plenty of possession whilst threatening, but offering few clear cut chances.
And so to penalties, at the same end in which the Reds won arguably the most famous penalty shoot-out of all time when lifting the European Cup against AC Milan in 2005.
Rickie Lambert, Adam Lallana, Emre Can and Joe Allen all responded with excellent penalties, as Besiktas buried all of their spot-kicks past Simon Mignolet.
It was left to Dejan Lovren to take the decisive kick with the score at 5-4 in the Turk’s favour, yet the Croatian blazed his effort over the crossbar, and saw the Reds eliminated from European competition in the process.