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.
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 on 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.
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