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How bad a season has it been for Man Utd? The worst ever? We look at other poor campaigns.
Defeat to old club Everton might be the most damning yet for the United boss, writes Daniel Storey.
Arsenal and Manchester United maintained their 100 per cent records in the UEFA Champions League, while Rangers drew with Barcelona.
Elsewhere across Europe, Lyon picked up their first win of the group phase with victory over Stuttgart.
Roma and Sevilla boosted their hopes of reaching the next round with wins at home over Sporting Lisbon and Steaua Bucharest respectively.
Arsenal were the biggest winners of the night as their imperious form continued with a thumping 7-0 victory over Slavia Prague at Emirates Stadium.
Cesc Fabregas got the ball rolling for Arsenal after just five minutes when he picked up a pass from Alexander Hleb and curled a superb shot beyond Martin Vaniak.
Arsenal were gifted the second goal on 24 minutes when David Hubacek diverted Hleb's shot into his own net.
Things got worse for Slavia four minutes before half-time when Theo Walcott capitalised on a poor clearance from Vaniak and slotted the ball into the net for his first Champions League goal.
Arsenal continued to run riot in the second half and Hleb got his name on the scoresheet six minutes after the break when he picked up a pass from Fabregas, cut his inside the full-back and slotted his shot past a bemused Vaniak.
The home side made it 5-0 four minutes later when they sliced Slavia open down the left and Walcott slid his shot in off the post.
Slavia could not live with Arsenal and Fabregas grabbed a sixth just before the hour mark with the goal of the night.
Arsenal broke from inside their own box through Hleb whose pass was dummied by Emmanuel Adebayor to Walcott and he played in Fabregas, to slide his shot past Vaniak and bring the home fans to their feet.
Substitute Nicklas Bendtner put the icing on the cake when he netted the seventh of the night, a minute from time, to complete a miserable evening for Slavia.
Sevilla picked up their second win in Group H with a hard-fought 2-1 win over Steaua Bucharest.
The home side got off to a flying start with Fredi Kanoute finding the net after just five minutes and Luis Fabiano added a second on 18 minutes when he rounded the keeper to score.
Steaua gave Sevilla a scare when Ovidiu Petre reduced the arrears on 64 minutes, but the home side held on for all three points.
Manchester United eased to a comfortable win over Dynamo Kiev in the Ukraine to put them on the brink of the knock-out stages.
Rio Ferdinand followed up his goal against Aston Villa last weekend with the opener on ten minutes with a powerful header from Ryan Giggs' free kick.
United doubled their lead eight minutes later when Rooney converted from close-range after Wes Brown's cross was deflected into his path.
Kiev gave themselves hope when Diogo Rincon rose highest at the far post to head the ball past Edwin van der Sar.
United restored their two-goal cushion four minutes before the break when Ronaldo headed home Giggs' cross.
Ronaldo netted his second of the night on 68 minutes when he converted from the penalty spot after Goran Gavrancic was adjudged to have handled inside the box.
Kiev made the scoreline more respectable 12 minutes from time when Ismael Bangoura found the bottom corner from the edge of the box.
In the other game in Group F, Roma beat Sporting Lisbon 2-1 at the Stadio Olimpico.
Juan headed Roma in front on the quarter hour mark, but the lead proved short-lived with Liedson drawing Sporting level just three minutes later.
Roma wasted the chance to restore their lead three minutes after the break when Mancini saw his penalty superbly saved by Tiago.
The home side grabbed the winner on 69 minutes when substitute Mirko Vucinic drove home from inside the box.
Rangers produced a battling performance to earn a goalless draw at home to Barcelona.
The Scottish side rode their luck in the first half at times as Barcelona dominated proceedings, but Allan McGregor stood up to everything the visitors could throw at him.
Rangers improved in the second half and Daniel Cousin missed a great chance to grab a winner ten minutes from time when he blazed his shot over the top.
The point keeps both sides locked on seven points at the top of Group E.
Lyon piled the misery on struggling Stuttgart with a 2-0 win in Germany to record their first victory in Group E.
The French champions broke the deadlock on 55 minutes when Fabio Santos scored with a deflected shot.
In-form striker Karim Benzema made the game safe for Lyon 11 minutes from time to condemn Stuttgart to their third successive defeat in the group.
Internazionale came from a goal down to beat CSKA Moscow 2-1 in Group G.
A terrible blunder by Veniamin Mandrykin gifted Internazionale the points as he somehow let Walter Samuel's header slip through his grasp.
CSKA Moscow stunned the Italians by going in front on 32 minutes, with Jo turning Ivan Cordoba inside the box and curling a superb shot over Julio Cesar.
Inter came out for the second half in determined fashion and drew level on 52 minutes with Hernan Crespo finding the net.
The Italians grabbed the winner ten minutes from time when Mandrykin made a mess of Samuel's header from Luis Figo's free kick.
In the other game in the group, ten-man Fenerbahce earned a goalless draw with PSV Eindhoven in a bad tempered affair at the Philips Stadion.
Deivid was sent off for Fenerbahce in the second half, but the Turks held on to secure a point and maintain their unbeaten start.
Barcelona had no answer. Swamped by Atletico Madrid’s pressing game, they were simply overwhelmed in a 20 minute onslaught.
It’s 10 years since Jose Mourinho took Porto to Champions League glory. It remains an incredible achievement, given added emphasis by the fact that the Portuguese club have only reached the quarter-finals once in the decade since.
Chelsea will have to overcome La Liga leaders Atletico Madrid to reach the Champions League final – but Alan Smith reckons Jose Mourinho will be happy with his side’s semi-final draw.
Read the thoughts and opinions of Jamie Carragher with skysports.com
Real Madrid's Cristiano Ronaldo says he misses Manchester United and will not celebrate if he scores against them.
Malaga have been banned from all UEFA club competitions for one season due to outstanding debts.
Celtic hope their Champions League showdown with Juventus can convince Victor Wanyama and Gary Hooper to sign new deals.
Malaga have vowed to appeal against the "disproportionate and unjustified" sanctions levied against the club by UEFA.
Malaga attacking midfielder Isco has been named Europe's best under-21 player of 2012.