Besiktas deservedly dumped Liverpool out of the Europa League Last 32 after Dejan Lovren missed the decisive penalty in Istanbul to hand the hosts a 5-4 shoot-out win after a 1-0 win in normal time.
The Reds produced an impressive performance in the first-half, enjoying the better of the game against a lacklustre Besiktas side. But roles were reversed after the break, and Brendan Rodgers' men were made to rue their missed chances when substitute Tolgay Arslan found the back of the net with a stunning strike from 20-yards in the 72nd minute.
Despite ramping up the pressure, Besiktas couldn't find a winner in normal time - with an extra half-an-hour needed to split the two teams. From 12-yards, both sides scored all nine penalties before Lovren stepped up to the fifth and sent it over the bar to knock his side out of European competition on the same pitch that Liverpool won the UEFA Champions League back in 2005.
The first 45 minutes was a dull affair, with chances few and far between. Liverpool were by far the better team, as they began to assert themselves more and more as time crept on despite a boisterous home crowd.
With a cacophonous atmosphere off of the field, Besiktas were just as keen to unsettle the visitors on the pitch - with Mario Balotelli going into the book inside 12 minutes for reacting angrily to a number of fouls committed against him.
But aside from that, the game never really exploded into life in the first-half. The first opportunity of the game came to Slaven Bilic's side, with the Turkish side doing well to work their way in behind a stubborn Reds' defence.
A low-cross from Olcay Şahan, intended for the prolific Demba Ba inside the six-yard box, forced Martin Skrtel to slide in and flick it away from danger.
Only minutes later up the other end, Liverpool's Raheem Sterling forced Cenk Gönen into a strong save after good work from the impressive Alberto Moreno down the left flank. The Spaniard, enjoying plenty of space, charged in towards the box but after a kind rebound, the ball fell invitingly for 20-year-old Sterling, but Gönen was on hand to palm his fierce half-volley to the left.
With the Reds growing in confidence, they began to dictate the tempo as they dominated possession for long periods.
Only a few minutes later, Sterling had another opportunity after striker Daniel Sturridge few him through on goal. A heavy touch allowed the ball to get away from the English international however, before there were no red shirts on hand to get on the end of his ball rolled across the box.
Sturridge himself, was far from at his best. After latching onto Kolo Toure's 50-yard pass downfield, he looked to be away on goal - but a poor touch allowed the ball to bobble away from control, before the move petered out to nothing.
But Brendan Rodgers' team continued to push forward. On the half-hour mark, Moreno again found joy down the left flank before cutting inside to find Sturridge. The striker, in turn, turned and played the ball to Sterling, whose shot earned a corner kick. Though the set-piece did not come to much, despite Joe Allen's delivery, as Martin Skrtel rose to send an always rising header over Gönen's crossbar.
With Besiktas sat back, struggling to really impact the game, they should have been one goal down after 34 minutes. Played through into space by strike partner Balotelli, Sturridge overcomplicated things by attempting to cut onto his left foot and after taking too much time, Gönen was able to push his side-footed effort away from danger.
Yet whilst they failed to find the net, Liverpool continued to pile on the pressure, as Moreno played a neat one-two with Sturridge before rushing his left-footed shot, which the home side's goalkeeper saved with relative ease.
Besiktas attempted to respond, having a rare opportunity to push upfield. Şahan produced the hosts' best effort of the first-half, coming inside from the left before firing a stinging shot towards the bottom corner, which Liverpool goalkeeper Simon Mignolet was equal to.
Despite not finding the breakthrough, Liverpool retained the advantage going into the break - courtesy of their 1-0 win in the first-leg.
With Besiktas having saw out a stalemate until half-time, they began to surge forward more frequently in the second 45 minutes, peppering Mignolet's goal with a few shots from range.
Evidently keen to attack more in the second-half, Besiktas' Ba and Atiba Hutchinson both tried their luck from outside the box but saw shots blocked. The ball then fell for Serdar Kurtuluş - whose shot stung the palms of Mignolet.
Slowly beginning to find their form, Argentine playmaker Sosa was the next to test the Belgian stopper, but Mignolet got down well to his effort destined for the bottom left.
Knowing a first goal would give them an equaliser on aggregate, the Istanbul side got a hold of the ball and began to bombard the English opposition. Ex-Chelsea youth prospect Gokhan Tore cut inside from the left dangerously, but could only curl a shot over Mignolet's bar.
Tore almost found himself with another opportunity, had it not been for an excellent sliding interception from the returning Kolo Toure, making his first start since his African Cup of Nations glory.
As the full-whistle drew nearer and nearer, Besiktas steadily stepped up their game - Tore getting the better of Toure near the by-line, before Skrtel hooked away his cross for a corner. The no.7 took the set-piece himself, but Balotelli was at the near post to clear.
Bilic's men continued to enjoy more of the ball, but couldn't carve any clear-cut opportunities. Shortly before the 70th minute, substitute Arslan almost found the goal they had been craving. Picking up the ball from the halfway line, the defender moved forward five or ten yards before unleashing a sensational strike that whistled narrowly wide of Mignolet's left-hand post.
Yet only a minute later, Arslan found the back of the net with a fantastic strike. After Tore drove inside from the left and found Ba, who turned to tee the substitute up outside of the box, Arslan curled a powerful right-footed effort inside of the top corner to level the tie.
With that, Liverpool found themselves in a precarious position. If they surged forward looking for a winner, the space they left behind could be exploited by the Turks - whilst if they sat back and played for extra-time, theyrisked inviting too much pressue upon themselves.
They opted for a mix, but Sterling could not pick out Sturridge after over-hitting his pass towards the byline with 14 minutes left. Besiktas, buoyed by their first goal, searched for a goal that could send them through, as substitute Javier Manquillo clumsily headed a simple header out for a corner, rather than back to his goalkeeper. Fortunately for the Spanish right-back, Hutchinson's effort from the corner was blocked and cleared.
The introduction of Manquillo, to help combact the threat of Tore down the left side, certainly helped quell the threat of the hosts - but Liverpool themselves were fairly toothless going up the pitch, having lost their momentum.
Rodgers, therefore, introduced Adam Lallana in place of Balotelli to help the offensive fluidity of his side. In the knowledge that a crucial Barclays Premier League clash against Manchester City awaited them this Sunday, the Reds began to regain a foothold of the game.
Lallana and Sturridge linked up with the former almost wriggling his way through inside the area, but they were soon outnumbered - before Ba dragged an ambitious 25-yard shot wide of goal on the counter-attack.
Goalscorer Arslan did exceptionally to beat Sterling, Toure and Manquillo with some skill - before winning a corner from the latter. Tore, swinging the following corner-kick into the six-yard box, found Ba but rather than find the back of the net, he could only rocket a strike off of the crossbar from close-range with the game needing exta-time to reach its conclusion.
Extra-time continued in much the same fashion as normal time ended, with Besiktas controlling the game as full-back Daniel Opare drilled a shot wide of the post in the 95th minute.
Frustrated by their abject second-half performance, Liverpool really struggled to reverse the flow of the game. Lallana and Moreno interchanged brightly down the left, before the substitute looked to have found his way in behind - but the ball bounced up awkwardly and deflected off his knee and out, summing up the Reds' form at that moment.
They were almost made to pay for a defensive error, when Joe Allen conceded possession cheaply. Besiktas soon found themselves on the shoulder of last man, but Mignolet got two strong hands to the striker's shot before Skrtel acrobatically cleared.
The Reds were nearly dealt a blow in the 100th minute, when Emre Can looked to have pulled up. Besiktas continued to play on, as Tore dropped his shoulder and beat two men - but his shot trickled along the surface meekly into Mignolet's grasp. Fortunately for the visitors, the German midfielder soon returned to the field despite the injury scare.
Sturridge who had been poor all evening, was replaced by Rickie Lambert in half-time of extra-time, as Rodgers kept penalties and the upcoming City game in mind. Though both sides were tiring as the quality of the game dropped considerably.
Sterling did well to win a free-kick out of Opare on the inside right channel, which Lallana sent in towards the red shirts inside the box, but it was too easily dealt with by the Besiktas defence.
With Liverpool looking to have settled for a penalty shoot-out on the same stadium in which the Reds won their fifth European Cup on penalties almost 10 years ago, Besiktas tried to find the winner - but Ba could only direct efforts over and wide in quick succession.
Neither side could find the decisive goal and as a result, the tie went the full length - to a penalty shoot-out.
The visitors, who had won five of their nine previous shoot-outs, three years to the day they won the Capital One Cup final on penalties, got off to a bad start as Ba sent Mignolet the wrong way. But profilic penalty-taker Lambert levelled it up, hammering his spot-kick past Gönen.
The lively Tore found the top corner with Besiktas' second penalty, putting the pressure on Lallana - but he handled it well, placing it to the goalkeeper's left. Besiktas continued their fine run of penalties, as Veli Kavlak sent his penalty beyond Mignolet and into the roof of the net. The 100% record from both sides continued, as German midfielder Can found the bottom corner perfectly despite the keeper guessing the right way.
Hutchinson was next up and sent another sensational penalty right into the top corner, a strike which Mignolet was never stopping despite going the same way. Liverpool's Allen equalled the calm composure of the Besiktas players, finding the top left corner.
With Besiktas' fifth, Arslan found the back of the net for the second time in the game - guiding his effort past Mignolet's fingertips, and with all the pressure on him, Dejan Lovren sent his penalty wide of the mark to put Besiktas through into the Last 16.