Liverpool lost their first European penalty shootout as Besiktas knocked them out of the Europa League.
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.
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.
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.