Liverpool came up just short as Chelsea, Tottenham survive. Elsewhere, holders Atletico Madrid crashed out
The five-time European champions exited on away goals at the hands of Russian outfit Zenit Saint Petersburg despite a 3-1 win at Anfield.
Two goals down from the first leg, Liverpool looked out for the count after veteran defender Jamie Carragher fluffed an attempted backpass and Brazilian Hulk slipped home the opener to make it 3-0 on aggregate for the visitors.
But Liverpool roared back with two goals from Luis Suarez with Joe Allen netting another in between, but the extra goal would not come as Zenit reached the last 16.
Liverpool manager Brendan Rodgers was defiant, saying: "We may have lost the battle tonight, but in terms of the war and going forward we're very much winning."