It wasn't a happy return to the Ataturk Olympic Stadium for Liverpool, the scene of their 2005 Champions League triumph, as this time the lottery of the penalty shootout went against them.
Liverpool were left to rue missed chances in the first half of the game, as they had the better of the play, while a well-worked goal from Tolgay Arslen finished them off as Besiktas were forced to try and find a way through from range, and eventually did.
Then it came to the penalty shootout which saw nine very well-taken efforts before centre-back Dejan Lovren stepped up to take the Reds' final spot-kick, only to miss the target and send Slaven Bilic's men through.
Brendan Rodgers now needs to regroup his side ahead of a massive game with Manchester City in the Premier League as the Reds looks to push for a place in the Champions League next season, and try and win the FA Cup.
Here is a selection of some of the best images from last night's action in Turkey: