DAVID 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 M
isimovic took the ball from his feet and rolled it into the net – although the England man partially atoned with a penalty save from the same player five minutes later.
Portsmouth's defeat and victory for Braga ensured Tony Adams' men cannot now qualify from Group E, while in contrast, Wolfsburg leapfrogged AC Milan to move into top spot.
Shell-shocked Pompey 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.
The visitors 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.
Amazingly, Adams' men then took the lead three minutes later when a neat passing 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.
It was very nearly three in the 20th minute but Defoe slid his shot inches wide from Traore's low cross.
The match was level again in the 23rd minute, however, when Gentner's low centre from the left evaded everybody and nestled into the net.
Sol Campbell was enduring a torrid evening and Dzeko ran off him to break clear minutes later but his effort was well wide. Defoe was then booked for a clumsy and late tackle on Andrea Barzagli.
The England striker was played in brilliantly by Johnson on the half-hour mark but he struggled to control the lofted ball and when he turned and shot from eight yards, his weak attempt was deflected wide.
The hosts then replaced limping full-back Cristian Zaccardo with Makoto Hasebe as the break approached. In the 42nd minute, James got down low to tip a well-placed Misimovic shot just past the post.
The second half began amid a cauldron of noise from a crowd of only 21,000, and Niko Kranjcar was within a whisker of restoring Pompey's lead with a 20-yard free-kick, which he curled brilliantly over the wall only to see it crash back off the crossbar.
The Croatian was becoming increasingly influential and he picked out Defoe in the box after a jinking run on the hour, but the defence smothered the danger.
Adams then decided to introduce Peter Crouch in place of Mvuemba as he sought a vital winning goal, but James gifted Wolfsburg the lead once again with a horrible mistake.
The England stopper attempted to dribble around Misimovic near the penalty spot, but the forward simply robbed him of the ball and rolled it into an unguarded net in the 74th minute.
Kanu was introduced for Kranjcar in a desperate bid to save the match. Five minutes later Campbell brought down Dzeko for a penalty, but James partially atoned with a parry from Misimovic's spot-kick, Johnson completing the clearance.
And with Wolfsburg content to play keep-ball for the remaining minutes, Pompey could not muster an equaliser, although even that would not have been enough to keep them in contention for a last-32 spot.
Wolfsburg: Benaglio, Riether (Madlung 46), Ricardo Costa, Barzagli, Schafer, Zaccardo (Hasebe 36), Josue, Dejagah (Simunek 88), Misimovic, Gentner, Dzeko. Subs Not Used: Lenz, Rodrigo Alvim, Saglik, Krzynowek. Booked: Schafer.
Portsmouth: James, Johnson, Campbell, Distin, Belhadj (Pamarot 46), Mvuemba (Crouch 66), Davis, Hughes, Traore, Kranjcar (Kanu 77), Defoe. Subs Not Used: Ashdown, Hreidarsson, Diop, Little. Booked: Defoe, Pamarot.
