Wolfsburg striker Zvjezdan Misimovic (R) runs past Portsmouth goalkeeper David James to score the third goal during their UEFA Cup match in Wolfsburg on Thursday. Photo: AFP
Portsmouth's first UEFA Cup campaign ended in heartbreak on Thursday with a 3-2 defeat at Wolfsburg which featured another embarrassing howler from England goalkeeper David James
Pompey surrendered a 2-1 lead in the Group E clash and their fate was sealed when Sporting Braga defeated Heerenveen 2-1 to secure the third qualifying place in the pool behind AC Milan and their German conquerors.
"I'm disappointed, we made mistakes, but Wolfsburg are a very good outfit," said Portsmouth boss Tony Adams.
Fellow English Premier League side Aston Villa made sure of their place in the last 32 despite suffering a shock 2-1 home defeat to Slovakia's MSK Zilina.
Their passage to the knockout round was assured when SV Hamburg defeated Slavia Prague 2-0 which allowed Ajax, who didn't play Thursday, to also qualify from Group F.
Portsmouth, who had squandered a 2-0 lead to draw 2-2 with AC Milan at Fratton Park last week, needed to win in Germany.
But Wolfsburg, with two wins from their first two games, were ahead after just three minutes when Edin Dzeko scored from Christian Gentner's right-wing cross.
Pompey then stormed into a 2-1 lead with Jermain Defoe finding the net from Armand Traore's cross in the 11th minute before Arnold Mvuemba scored with a long distance drive three minutes later.
Gentner then levelled for Wolfsburg after 23 minutes with Zvjezdan Misimovic hitting the decisive third in the 74th minute after a terrible mistake by James.
The England stopper gifted the goal when he allowed Misimovic to take the ball off his feet and roll it into the net.
James then partially made amends when he saved an 80th-minute Misimovic penalty which was awarded when Sol Campbell chopped down Dzeko.
Adams refused to criticise James.
"David is a fantastic goalkeeper, he's saved us penalties and he has set up the first goal," said the manager. "I've got great faith in him and I love him to bits."
Croatian duo Ivica Olic and Mladen Petric, with a last-minute penalty, gave Hamburg, coached by former Spurs boss Martin Jol, their 2-0 win in Prague.
That was a blessing for Martin O'Neill's Aston Villa who fell behind to goals from MSK Zilina's Vladimir Leitner, who was later sent off, and Peter Styvar.
Nathan Delfouneso pulled one back on his full debut for Villa.
"I don't think we started well enough and we made silly mistakes and from then on it was going to be an uphill struggle," said Villa midfielder Nigel Reo-Coker.
Brazilian striker Vagner Love hit a hat-trick as CSKA Moscow, the 2005 UEFA Cup winners, made it four wins in four with a 4-3 win at French side Nancy in Group H.
In Group G, St Etienne, who have already qualified, were joined in the last 32 by Valencia after the Spanish side's 1-1 home draw with Club Bruges.