On a bad night for British sides in the Champions League Chelsea, Celtic and Manchester United all slumped to defeat.
Chelsea's Champions League hopes are hanging by a thread after going down 3-0 to Juventus in Turin.
Juventus made the breakthrough seven minutes before half-time when Andrea Pirlo's shot deflected off Fabio Quagliarella to wrongfoot Petr Cech in the Chelsea goal and although the keeper got a hand on the ball he could not stop it crossing the line.
Juventus doubled their lead just past the hour mark when Kwadwo Asamoah cut the ball back for Arturo Vidal and his shot took a deflection off Ramires before flying through Cech's legs.
The Italian champions piled the misery on Chelsea with a third goal in stoppage time as Sebastian Giovinco beat Cech to a through ball to slide the ball under the keeper to leave the Blues on a knife edge in their final game against Nordsdjaelland.
The holders need to beat Nordsdjaelland at Stamford Bridge and hope Shakhtar Donetsk can do them a favour against Juventus otherwise they will become the first defending champions to go out at the group stages.
Shakhtar Donetsk booked their place in the knockout stages with a controversial 5-2 win over Nordsdjaelland in Denmark.
Morten Nordstrand gave the Danes the lead after 24 minutes, but the game erupted into controversy two minutes later when Adriano levelled matters in extraordinary circumstances.
Willian played a drop ball back Nordsdjaelland after an injury with the home side expecting the ball to run through to their goalkeeper only for Adriano to take the ball and round the shot-stopper to score.
The goal provoked angry reactions from Nordsjaelland players with the Danes expecting Shakhtar to allow them to score from the resulting kick-off, but the Ukrainians refused.
Nordsjaelland did restore their lead on the half hour mark when Kasper Lorentzen found the net, but Willian hit back for Shakhtar on the stroke of half-time.
Shaktar took control of the game early in the second with two goals in three minutes from Willian (50) and Adriano (53) to put the game beyond Nordsjaelland.
Public enemy No.1 Adriano completed his hat-trick nine minutes from time to pile the misery on the hosts.
Celtic's fate will go down to the final game after they went down to a 2-1 defeat to Benfica at the Estadio da Luz.
Knowing a score draw would be enough to send them through Celtic got off to the worst possible start when they failed to clear a ball into their box and the ball dropped to Ola John who drilled his shot past Fraser Forster.
The Scottish champions drew level on 32 minutes when Charlie Mulgrew's corner found Georgios Samaras unmarked at the far post and the Greek striker headed home from close range.
After a prolonged period of pressure Benfica restored their lead 19 minutes from time when Luisao headed the ball into the path of Ezequiel Garay to volley home past Forster.
The defeat means Benfica will head into the final round of matches needing to just equal Celtic's result in their final game to deprive the Bhoys of a place in the last 16.
Barcelona cruised into the last 16 with a 3-0 win over Spartak Moscow in a freezing Russia.
Lionel Messi scored twice to bring his tally to 80 goals during this calendar year with Dani Alves netting the other for the Spanish giants.
Alves broke the deadlock after 12 minutes with a superb half-volleyed effort from the edge of the box.
Messi doubled the lead on 27 minutes when Andrei Dykan could only parry Andres Iniesta's shot and the Argentine pounced on the rebound to scuff his effort into the ground before bouncing into the net.
Barcelona put the game beyond Spartak six minutes before the break when Pedro sent Messi clear on goal and the little magician rounded Dykan before slotting the ball into the empty net.
A youthful Manchester United side lost 1-0 to Galatasaray in Istanbul as Sir Alex Ferguson saw his side's 100 per cent record in Group H come to an end.
United went close to opening the scoring at the end of the first half when Nick Powell headed Tom Cleverley's corner against the crossbar.
Burak Yilmaz broke the deadlock for Galatasaray on 54 minutes when he headed home from a corner past Anders Lindegaard just seconds after the keeper had made a great save to keep out a point-blank Felipe Melo header.
Cluj's Portuguese striker Rui Pedro scored a first half hat-trick to inspire the Romanian side to a 3-1 win over Braga.
Cluj raced into a 2-0 lead thanks to strikes from Pedro (7,15), but Alan reduced the arrears two minutes later for Braga.
Pedro completed his treble on 33 minutes and things got worse for Braga just before the interval when Douglao was red carded.
In Group F Bayern Munich and Valencia both qualified for the knockout stages after a 1-1 draw in the Mestalla.
Valencia were reduced to 10 men on 33 minutes when defender Antonio Barragan was sent off for the home side.
However, despite their disadvantage Valencia went in front 13 minutes from time with Sofiane Feghouli getting his name on the scoresheet.
The lead proved short-lived as Thomas Muller levelled matters for Bayern on 82 minutes.
Valencia had already booked their place in the last 16 before even kicking a ball after BATE Borisov lost 2-0 at home to Lille.
Lille, who had failed to pick up a point prior to the game, broke their duck to hit BATE's hopes of progressing.
First half goals from Djibril Sidibe and Gianni Bruno were enough to give the French side the three points, but Sidibe soured his evening's work by getting sent off 15 minutes from time.