Champions League Group F: Napoli 2 Arsenal 0

Ten-man Arsenal squeezed into the last 16 of the Champions League – but defeat at the Stadio San Paolo cost them top spot in Group F.

The Gunners held out until the 73rd minute, when Gonzalo Higuain fired Napoli in front – and they suffered a second blow when captain Mikel Arteta was sent off soon afterwards.

Although Jose Callejon added a second goal in injury time, Borussia Dortmund’s late winner in Marseille consigned the unlucky Italians to Europa League football in the new year.

The result also meant that the Gunners had to settle for the runners-up spot in the group behind Dortmund – and they will go into Monday’s draw for the knockout stages as an unseeded side.

With the onus on the home side to force the pace, they adopted a policy of pressing Arsenal high up the pitch, but created few actual openings in the first half.

Goran Pandev drove straight at Wojciech Szczesny, while Callejon cut inside and fired over the bar – but, for the most part, Per Mertesacker and Laurent Koscielny looked unruffled.

There were a couple of brief scares for the Gunners late in the first half as Higuain’s ball opened up the defence and Christian Maggio gave chase, clipping his attempt over Szczesny and just wide of the target.

Soon afterwards Szczesny was too casual with a Koscielny back-pass, presenting the ball to the head of a surprised Higuain, but the rebound flew behind.

In fact, it was Arsenal who carved out the best opening of the first half as Mesut Ozil and Mathieu Flamini combined to set up Olivier Giroud, but his left-foot shot was beaten away by Rafael Cabral.

Napoli stepped up the pace after the restart, introducing the tricky Lorenzo Insigne on the left-hand side and beginning to put the Gunners under longer spells of pressure.

Left-back Pablo Armero burst into the penalty area, only to bundle his shot into the hands of Szczesny, while Callejon took advantage of a slip by Koscielny but dragged the chance wide.

Higuain also blazed an opportunity over – but it was the former Arsenal target who broke the deadlock soon afterwards, collecting Callejon’s pass and turning Mertesacker to drill a low finish past Szczesny.

The home supporters’ spirits were lifted even further three minutes later when Arsenal were reduced to 10 men, with Arteta shown his second yellow card of the game for a lunge on Callejon.

The Gunners conceded again with just seconds remaining in added time as Callejon reached Insigne’s cross and lobbed Szczesny – but it was not quite enough to send Napoli through at their visitors’ expense.

Arsenal: Szczesny; Jenkinson, Mertesacker, Koscielny, Gibbs; Flamini, Arteta; Rosicky (Monreal 75), Ozil, Cazorla (Ramsey 67); Giroud.