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A horrendous error from David James saw Portsmouth crash to a 3-2 defeat at Bundesliga side Wolfsburg which ends their interest in this season's UEFA Cup.

Portsmouth still have one match left to play in Group E but can no longer qualify after picking up just one point from their opening three games.

There were still in the mix with 15 minutes to go with the sides level at 2-2, but James then inexplicably side-footed a back pass straight into the path of Zvjezdan Misimovic, who rounded the England keeper and slotted the ball into the empty net.

James saved a woeful penalty from the same player five minutes later but by then the damage was done, with Pompey being unable to find a way back into the match.

Goals from Jermain Defoe and Arnold Mvuemba helped Portsmouth go from 1-0 down to 2-1 up in a pulsating opening before Christian Gentner made it 2-2 in just the 23rd minute.

Wolfsburg had taken the lead after just three minutes when the Portsmouth defence was caught napping.

Sol Campbell allowed Bosnian striker Edin Dzeko to ghost in behind him and casually side foot past James after Gentner had whipped a cross in behind the defence, despite being surrounded by blue shirts on the edge of the area.

Pompey, however, levelled in just the 11th minute and it was James who set up the attack with a fabulous long throw that set Armand Traore free down the left.

Traore then crossed into the box forcing Wolfsburg keeper Diego Benagilo into a dive to push it away, but the ball went into the path of Defoe who showed great balance to direct the ball into the empty net.

Just three minutes later and the noisy away supporters were ecstatic as Pompey took the lead.

A spell of crisp passing from the visitors eventually freed up room for Mvuemba to try his luck from distance and helped by a deflection off Andrea Barzagil the ball flew into the top corner.

Defoe pulled a half chance just wide not long after, but then in the 23rd minute Wolfsburg again punished sloppy defending as Gentner's low curled cross missed everybody in the box and nestled into the corner of the net as a flat footed James could only look on.

Defoe nearly gave Pompey back the lead in the 31st minute before being crowded out, while at the other end James had to get down low to fingertip away a low Mismovic drive. At the break the sides were level 2-2.

The second-half was a much more timid affair than the first but Portsmouth nearly went back in front when Niko Kranjcar curled a great free-kick over the wall, only to then see his shot hit the underside of the bar.

With both sides now looking solid it seemed like only a mistake or a moment of brilliance would produce a winner and, unfortunately for Portsmouth, James's howler ensured it would be the former scenario.

In the 80th minute Campbell clumsily brought down Dzeko in the box but Misimovic scuffed his chance to clinch the match as James saved with ease.

But the miss did not prove costly as Portsmouth, who put substitutes Peter Crouch and Nwankwo Kanu alongside the previously lone striker Defoe, failed to create any late chances.

Instead, Tony Adams's side suffered another late below when Traore was forced off with what looked like a hamstring injury just before the end.

Seán Fay / Eurosport