Roberto Di Matteo went from Champions League hero to zero as Chelsea crashed to a 3-0 defeat at Juventus and to the brink of an embarrassing exit from the competition.
Di Matteo's biggest selection gamble since he took charge backfired as goals from Fabio Quagliarella, Arturo Vidal and Sebastian Giovinco left the Blues facing the prospect of becoming the first holders to depart the competition before Christmas.
Chelsea slumped to third place in Group E with one match remaining and must win against Nordsjaelland in two weeks' time and hope Shakhtar Donetsk beat Juve, despite the Ukrainian side having qualified for the last 16 themselves tonight.
A hat-trick by Adriano and two goals from Willian saw Shakhtar Donetsk go through to the knockout stages of the Champions League following a 5-2 win at Nordsjaelland.
In a see-saw game full of controversy, the Danish hosts twice went ahead before the game was level at half-time.
However, Shakhtar were dominant after the break to run out eventual winners in Copenhagen, going a point clear of Juventus at the top of Group E.
Nordsjaelland certainly played their part in the game but had nothing to show at the end of the night and still have just one point from five games after an abortive European campaign.
BATE Borisov's 2-0 home defeat to Lille secured Valencia's passage. It was Lille's first win of a demoralising campaign.
The Ligue 1 side had not taken a single point from their first four matches and had a negative goal difference of 12 going into the clash against Belorussian champions. But they scored twice in the first half through Djibril Sidibe and Gianni Bruno and held on without conceding despite Sidibe being sent off with 15 minutes remaining.
A 1-1 draw at the Mestalla ensured both Valencia and Bayern Munich booked their place in the knockout stage of the Champions League.
BATE Borisov's earlier defeat to Lille left each side within a point of progressing and they duly shared the spoils, despite the Spanish side losing Antonio Barragan to a red card after only 33 minutes.
Indeed it was Valencia who opened the scoring, Sofiane Feghouli finding the target in the 77th minute only for Thomas Muller to draw the Bundesliga giants level five minutes later.
Lionel Messi moved to within five goals of Gerd Muller's scoring record as Barcelona qualified for the knockout stages of the Champions League with an easy 3-0 victory over Spartak Moscow.
Messi scored twice to go to 80 goals so far in 2012, just five behind Muller's record number of goals scored in a calendar year from 1972. Dani Alves gave Barcelona the lead before Messi's double strike with all the goals coming before half-time.
Celtic's bid to win through to the knockout stages of the Champions League will go to their last Group G fixture following their 2-1 defeat by Benfica at the Stadium of Light.
Ola John gave the home side the lead in the seventh minute before Georgios Samaras levelled in the 32nd minute from a Charlie Mulgrew corner.
Defender Ezequiel Garay restored Benfica's lead in the 72nd minute to ultimately, and deservedly, leave both sides on seven points after five games.
The Scottish champions, guaranteed a Europa League spot after Barcelona beat Spartak 3-0 in Moscow earlier in the evening, will go through if, in their home game against the Russian club, they better the Portuguese side's result in Barcelona.
Manchester United got burned once more on their return to 'Hell' as Galatasaray ended their 100% record in Champions League Group H with a 1-0 win.
Burak Yilmaz's second-half goal was enough to give the Turkish side a deserved victory and take them to the brink of qualification for the knockout stage.
United's position in the last 16 was already confirmed so the damage, beyond any sustained as a result of the ear-splitting din, cannot be compared to the tumult that unfolded on United's first meeting with Galatasaray in Istanbul 19 years ago.
A first-half Rui Pedro hat-trick fired CFR Cluj closer to a first-ever appearance in the Champions League knockout stage following a comfortable 3-1 win over 10-man Braga.
Portuguese striker Rui Pedro ended the qualifying hopes of his countrymen during a scintillating opening first half in which the beleaguered visitors also had Douglao sent off.
Rui Pedro had his treble within 33 minutes and, while Alan had pulled a goal back on 17 minutes, Cluj were in full control by the break once Douglao saw red in added time.
While Cluj failed to add to their tally, victory ensured they moved level with Galatasaray with a game remaining in Group H.
The Romanians face United at Old Trafford on the final matchday with Gala travelling to Braga.