Manchester City were emphatically beaten by Hamburg in the first leg of their quarter-final to leave their Uefa Cup hopes hanging by a thread.
Stephen Ireland slotted the visitors ahead after 35 seconds but they were under constant pressure after that.
Joris Mathijsen headed Hamburg level before Piotr Trochowski converted a penalty after Micah Richards' handball.
Jose Paolo Guerrero then fired in from close range at the far post to put the German side firmly in the driving seat.
The home side would have been in an even stronger position had it not been for City keeper Shay Given's heroics as the visitors' defensive frailties away from home were again exposed.
Hamburg boss Martin Jol would have been confident about the chances of his joint Bundesliga leaders ahead of the game, especially as he had won all six of his games against City while in charge of Tottenham.
Hamburg: Rost, Benjamin, Gravgaard, Mathijsen, Jansen, Pitroipa, Jarolim, Aogo, Trochowski, Petric, Olic (Guerrero 71).
Subs Not Used: Hesl, Ndjeng, Rincon, Schmidt, Torun.
Booked: Trochowski, Pitroipa.
Goals: Mathijsen 9, Trochowski 64 pen, Guerrero 79.
Man City: Given, Richards, Dunne, Onuoha, Bridge (Garrido 46), Wright-Phillips (Fernandes 83), Zabaleta, Ireland, Sturridge (Mwaruwari 62), Bellamy, Robinho.
Subs Not Used: Hart, Elano, Petrov, Berti.
Booked: Bellamy, Given.
Goals: Ireland 1.
Att: 50,500
Ref: Olegario Benquerenca (Portugal).
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