A Jamie Carragher error ultimately proved costly as Liverpool were edged out of the Europa League on away goals despite a fine comeback against Zenit St Petersburg.
The veteran defender, making his 150th - and now last - European appearance, gifted Zenit's star forward Hulk a goal that gave the Russians a 3-0 aggregate lead early in the second leg of the last-32 tie.
Liverpool responded as top scorer Luis Suarez fired in two free-kicks and Joe Allen struck from close range but Hulk's vital away goal prevented another memorable Anfield fightback.
Substitute Eden Hazard saved Chelsea's blushes with a stoppage-time strike that saw Rafael Benitez's side sneak into the Europa League last-16 at the expense of Sparta Prague after securing a 1-1 draw.
Just nine months on from winning the Champions League, the west Londoners only just managed to overcome the side third in the Czech top flight at Stamford Bridge. They will now face Steaua Bucharest who overcame Dutch giants Ajax on penalties.
Tottenham's difficult week in Lyon ended on a dramatic high after Mousa Dembele fired his team in to the last 16 of the Europa League with a stunning last-minute strike to grab a 1-1 draw.
Maxime Gonalons, the Lyon captain, looked to have fired Lyon to the 1-0 win they required to advance with his first-half goal.
However, Dembele popped up in the 90th minute, hammering a blistering 25-yard strike past Remy Vercoutre to set up a mouth-watering third round tie against Inter Milan.
Shola Ameobi fired Newcastle into the last 16 of the Europa League from the penalty spot as the Magpies kept their cool to beat Metalist Kharkiv 1-0 in icy Ukraine.
Ameobi's 15th European goal - only Alan Shearer has scored more for the club - came after midfielder Moussa Sissoko had been tripped by goalkeeper Olexandr Goryainov. The striker calmly converted from 12 yards to silence a packed house at the Metalist Stadium. They will now face Anzhi who drew 1-1 with Hannover but won 4-2 on aggregate.
Holders Atletico Madrid were knocked out of the Europa League at the last-32 stage despite defeating Rubin Kazan 1-0 at the Luzhniki Stadium in Moscow.
A goal by Radamel Falcao in the 84th minute gave the visitors hope of overturning the two-goal deficit from the first leg at the Vicente Calderon last week.
However, despite playing with a man extra in the final minutes of the game after Rubin Kazan captain Cesar Navas was sent off, they were unable to score again.
Levante will now meet Rubin after an early goal by Obafemi Martins set up a comfortable 1-0 victory over Olympiakos in Athens.
Inter Milan eased the pressure on under-fire coach Andrea Stramaccioni as Colombian midfielder Fredy Guarin scored twice to see off Romanian side Cluj 3-0 in the last 32 of the Europa League.
Stramaccioni's position had come under increased scrutiny after a 4-1 defeat to Fiorentina on Sunday had left Inter with just one win in five Serie A games.
But Guarin netted twice and Marco Benassi scored a late third as Cluj were forced to play the final 10 minutes with 10 men following the sending off of Mario Camora.
Lazio comfortably progressed to the last 16 of the Europa League after first-half goals from Antonio Candreva and Alvaro Gonzalez downed Borussia Monchengladbach 2-0.
The two sides drew 3-3 in last week's barnstorming first leg, in which the German side were awarded three penalties and Lazio grabbed a stoppage-time equaliser.
It looked as though another evening of excitement was in prospect when Candreva sidefooted the hosts in front inside 10 minutes after dispossessing defender Alvaro Dominguez. But Gonzalez's goal shortly after the half-hour was enough to seal a routine win on the night and a 5-3 aggregate scoreline to set up a tie against another Bundesliga side, Stuttgart.
Stuttgart put their dismal domestic form to one side and eased into the last 16 of the Europa League with a 2-0 victory over Genk.
Goals from Arthur Boka and Christian Gentner made it all seem fairly straightforward for the Bundesliga side, who arrived with question marks hovering over them after only ending a run of five straight league defeats by beating Hoffenheim 1-0 at the weekend, while a 1-1 draw in the first leg left this tie delicately poised.
Basel progressed through to the last 16 of the Europa League after holding Dnipro to a 1-1 draw in a match which saw both teams net late penalties and finish with 10 men.
A solitary goal by Cheick Diabate shortly before half-time was enough to guide Bordeaux to a 1-0 win against Dynamo Kiev. Diabate struck home a low shot in the 41st minute to give the Ligue 1 side a 2-1 aggregate victory.
Cristian Baroni's first-half penalty was enough to give Fenerbahce a 1-0 victory over 10-man BATE Borisov where they will meet Viktoria Plzen who convincingly defeated Serie A title hopefuls Napoli 2-0 to book their place in the last 16 of the Europa League for the first time.
Plzen raised eyebrows all over Europe as they cantered to a 3-0 win in Naples last week and completed a professional performance over two legs with an impressive victory on home soil to set up a meeting with Fenerbahce in the next round.
Brazilian goalkeeper Artur was in fine form for Benfica as they beat Bayer Leverkusen 2-1 to progress in the Europa League.