Wolfsburg 3 Portsmouth 2DAVID JAMES' howler sent Portsmouth crashing out of Europe as they tumbled to a heart-breaking Uefa Cup defeat in Wolfsburg.

Edin Dzeko fired the hosts into an early lead before Pompey hit back through Jermain Defoe and Arnold Mvuemba, although Christian Gentner levelled things up before the break.

James then gifted the Germans a third in the 74th minute when Zvjezdan Misimovic took the ball from his feet and rolled it into the net - although the England man partially atoned with a penalty save five minutes later.

Portsmouth's defeat and victory for Braga last night ensured Tony Adams' men cannot now qualify from Group E, while in contrast, Wolfsburg leapfrogged AC Milan to move into top spot.

Adams opted for one man in attack as Defoe was asked to go it alone up front. That meant Peter Crouch was dropped to the bench as Mvuemba came in to bolster the midfield alongside Niko Kranjcar.

The visitors were a goal down in the fourth minute when Gentner showed neat skill on the right and crossed low for Bosnian Dzeko to flick home from close range.

But they were level in the 11th minute after a brilliant counter-attack instigated by James' early throw to Armand Traore following a Wolfsburg corner. The Frenchman surged down the left and clipped in a cross that Diego Benaglio could only palm to Defoe, who scuffed his shot with just enough power to creep over the line.

Adams' men then took the lead three minutes later when a neat move involving Glen Johnson and Sean Davis saw the ball end up with Mvuemba, who placed a shot into the corner of the net from 20 yards, with the help of a deflection.

The match was level again in the 23rd minute when Gentner's centre from the left evaded everybody and nestled into the net.

WOLFSBURG: Benaglio, Riether (Madlung 46 mins), Costa, Barzagli, Schäfer, Zaccardo (Hasebe 36 mins), Josué, Dejagah (Šimunek 88 mins), Misimovic, Gentner, Dzeko. Subs not used: Lenz, Alvin, Saglik, Krzynówek. Booked: Schafer. Goals: Dzeko 3, Gentner 23, Misimovic 74.

PORTSMOUTH: James, Johnson, Campbell, Distin, Belhadj (Pamarot 46 mins), Mvuemba (Crouch 66 mins), Davis, Hughes, Traoré, Kranjcar (Kanu 77 mins), Defoe. Subs not used: Ashdown, Hreidarsson, Diop, Little. Booked: Defoe, Pamarot. Goals: Defoe 11, Mvuemba 14.

Referee: Ivan Bebek (Croatia).