Centre-back Dejan Lovren missed the crucial spot-kick after Tolgay Arslan's 20-yard curler forced extra-time in the round of 32 second leg.

Daniel Sturridge's shot was beaten out by Cenk Gonen as Liverpool failed to make their first-half superiority tell.

Besiktas were the better side after that, and almost sealed the tie in 90 minutes as Demba Ba hit the crossbar.

Liverpool had happy memories of their last penalty shootout at the Ataturk Olympic Stadium, where they beat AC Milan to win the 2005 Champions League, but there was to be no repeat here.

Slaven Bilic's side deserved to go through after recovering from a dreadful opening 45 minutes to dominate the game, meaning that Liverpool are left with the FA Cup as their last realistic hope of a trophy this season.

Mario Balotelli played for 82 minutes as he made his first Liverpool start since 8 November, and largely managed to hold his discipline despite an early booking for a foul on Veli Kavlak.

Liverpool were missing a number of injured key players - including captain Steven Gerrard, vice-captain Jordan Henderson, centre-back Mamadou Sakho and playmaker Philippe Coutinho.

But they should have made more of a number of first-half chances, as Raheem Sterling had a shot beaten away somewhat theatrically by keeper Cenk Gonen, then saw a shot on the turn deflected wide by Necip Uysal after Alberto Moreno and Daniel Sturridge had combined to set him up.

(BBC)