Valeri Bojinov and Martin Petrov were left dejected by City's shock defeat
Manchester City suffered a humiliating home defeat by Danish side FC Midtjylland in the first leg of their Uefa Cup second qualifying round tie.
The Danes took the lead on 15 minutes when Danny Olsen punished Richard Dunne's mistake with a precise finish.
City had made a dreadful start but did improve and Daniel Sturridge smashed a shot against the bar before half-time.
Martin Petrov also hit the woodwork with a late free-kick but City could not turn their possession into chances.
Mark Hughes's side will still fancy their chances in the return leg in a fortnight's time but they will need to find a greater cutting edge in Denmark if they are to get the win they need to progress.
City have had a difficult summer off the pitch because of the charges of corruption and abuse of power that their owner Thaksin Shinawatra faces in Thailand and this game highlighted their on-field problems too.
Hughes, who had to speak out this week to quell fears that players were being sold without his knowledge because of the uncertainty surrounding Thaksin, must turn things round ahead of City's opening Premier League game against Aston Villa on Sunday.
He has already returned to his former club Blackburn to bid, unsuccessfully, for Paraguyan striker Roque Santa Cruz and this game showed why he is so keen to add to his depleted strikeforce.
With three senior strikers - Jo, Benjani Mwaruwari and Darius Vassell - all unavailable, Hughes was forced to pair two teenagers up front in Felipe Caicedo and Sturridge against the Danes.
The duo made an uncertain start and City's lack of presence in attack, combined with some woefully inaccurate passing, put them on the back foot in the early stages.
Midtjylland began to come forward with purpose but despite the home side's lethargy it was still a surprise when the visitors took the lead.
Dunne, whose distribution had been poor from the start, gave the ball away and Mikkel Thygesen found Olsen, who produced a stunning finish.
The goal stunned City and their fans but it at least served to wake Hughes' side from their slumbers and they almost managed an instant reply when Petrov's chip sailed over the bar.
And, although Caicedo continued to look too cumbersome to trouble the visitors defence, Sturridge did eventually begin to threaten.
Danny Olsen celebrates with Kolja Afriyie after scoring Midtjylland's winner
After scuffing his first two efforts of the night, an attempted volley and a shot from 30 yards, Sturridge produced City's best effort when he smashed the ball against the underside of the bar from the edge of the area.
City continued to come forward after the break and Petrov should have done far better when he volleyed hopelessly high and wide after Elano picked him out in the area.
Elano fired wide himself soon afterwards but, with the Danes defending in numbers, chances for City soon began to dry up.
Although Michael Johnson tested Lasse Heinze with a powerful shot and Petrov floated a free-kick on to the bar before the end, Midtjylland were hardly hanging on.
In fact, they could easily have extended their lead when George Florescu broke clear late on but Joe Hart produced a fabulous save to deny him.
The handful of visiting fans at Eastlands celebrated what was a famous victory at the final whistle and the result leaves Hughes with plenty to chew on.
Manchester City boss Mark Hughes:
"Perhaps we were a bit behind them in terms of sharpness and match fitness but that is no excuse.
"In the first half we had too many unforced errors. We needed to be more dynamic, show more personality, and to try to drive the play.
"We need to get up to speed before the weekend and hopefully this game will let us know where we are at and what we need to do."
Midtjylland defender Danny Calliff:
"We had to believe that we could get a result. We had to match the effort and tonight it was enough.
"I think at the start of the match they didn't expect us to come out and take it to them with the energy and effort that we showed.
"We expected them to come back at out ground and not underestimate but we'll have out fans behind us and we believe we can do it."
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