Arsenal were forced to settle for second place in Champions League Group G after slumping to a lacklustre 2-0 defeat at Porto on Wednesday.
Arsene Wenger's side needed only a draw at the Dragao Stadium to guarantee pole position and the advantage of a home second leg tie in the second round.
But Wenger put out an under-strength team and paid the price as his youngsters were swept aside by the Portuguese champions.
Bruno Alves punished poor defending to open the scoring just before half-time and Lisandro Lopez lashed in the second soon after the interval.
The defeat was Arsenal's first of the group stages but, with Barcelona, Bayern Munich and Roma among the potential group winners lying in wait in the last 16, it could prove fatal to their chances of advancing to the latter stages.
“We were quite comfortable until they scored, what was disappointing was when we tried to come back we were not capable of creating chances. We gave the ball away and were in danger of conceding more,” Wenger said.
“Many players had little injuries and in the Premier League we are in a position when every game is vital and that's what we tried to protect this week.
“It will be difficult in the next round but we will be up for it and we have a chance against any side in the world.”
Manuel Almunia, Arsenal's stand-in skipper, added: “We were not in the game at any moment, we were not aggressive, we didn't pass the ball well and this is why we lost.
“I'm very disappointed. Everyone is wearing the Arsenal shirt and has to give 100 percent. That was not the case.”
Wenger made seven changes to the team that defeated Wigan on Saturday and Emmanuel Eboue was given a chance to silence the boo-boys who jeered him off after a woeful substitutes' appearance.
But Wenger was without injured midfielders Cesc Fabregas and Samir Nasri and opted to rest Emmanuel Adebayor and Robin van Persie.
Eboue was back in the travelling Arsenal fans' good books before the game as they chanted his name, but he still looked nervous in the early stages and fouled Porto striker Hulk on the edge of the area.
Bruno Alves's resulting free-kick forced a smart stop from Almunia.
Arsenal threatened for the first time when Mexican teenager Carlos Vela won a free-kick and Denilson's deep set piece was headed over by Abou Diaby.
A neat combination between Nicklas Bendtner and Aaron Ramsey opened up the Porto defence in the 25th minute. Welsh teenager Ramsey cut into the penalty area, turned his marker and fired in a low shot, which Helton did well to push around the far post.
But that was as good as it got for Arsenal in the first half though. They lacked any drive or attacking momentum and Porto were able to wrestle control of midfield with little resistance.
Almunia had to rescue the Gunners when he blocked Lucho Gonzalez's close-range effort and Gallas was on hand to scramble the loose ball clear.
Porto stepped up the pressure and got their reward in the 39th minute as Diaby was punished for a dismal piece of defending.
Diaby completely lost Bruno Alves at an inswinging corner and the Arsenal midfielder could only watch in dismay as the Porto star headed powerfully past Almunia.
Arsenal were just as lethargic after half-time and it was Eboue who was the villain again as the right-back's dozy defending allowed Lisandro to make it 2-0 in the 54th minute.
Fernando's pass split the Arsenal defence but Eboue played Lisandro onside and the striker took full advantage, racing clear to drive past Almunia.
Wenger responded by sending on teenagers Kieran Gibbs and Jack Wilshere and Arsenal briefly showed some life when Ramsey's turn and shot tested Helton.
Porto still looked the more potent force and Cristian Rodriguez made a dynamic run into the area that ended with a low shot just wide of the far post.
Lucho should have added to Arsenal's misery but failed to hit the target with only Almunia to beat. Wenger and company had to be content with such small mercies on a dispiriting night.
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