SEVILLA - Arsenal lost their long unbeaten record and top spot in Group H after slumping to a Champions League defeat by a dominant Sevilla on Tuesday night.
Arsenal had not been beaten in a competitive match since the start of April, but goals from Seydou Keita, Luis Fabiano and former Tottenham striker Fredi Kanoute saw victorious Sevilla join the already-qualified Gunners in progressing through to the last 16.
Eduardo Da Silva scored for Arsenal but it was not enough to save Arsene Wenger's men, and they will need to beat Steaua Bucharest in their final match and hope Sevilla slip up against Slavia Prague to clinch first place.
The two teams went into the match at the Ramon Sanchez-Pizjuan with starkly contrasting domestic records this season.
Arsenal are unbeaten and boast a three-point lead at the top of the Premier League table, while Sevilla have lost seven of their 12 La Liga matches and already find themselves 14 points adrift of pacesetters Real Madrid.
Sevilla had also lost their last two league games and suffered a 3-0 defeat at the hands of Arsenal in the opening round of group matches, but Manolo Jimenez's side were faster out of the blocks tonight with Kanoute going close early on.
Arsenal, with seven changes to the side that started against Wigan at the weekend, barely threatened in the opening stages, but with their first serious attack in the 11th minute they managed to take the lead.
Nicklas Bendtner sent in a cross from the right which found Eduardo lurking between two Sevilla defenders, and the Croatian showed good chest control before slotting the ball home at the far post.
It was the ideal start to the match for the Premier League leaders but that advantage did not last long as Sevilla drew level in the 24th minute with a superb strike from midfielder Keita.
A fluffed clearance by Philippe Senderos gifted Jesus Navas possession on the right and although his low cross was cleared by Gilberto, Keita was on hand to rifle a stunning 20-yard shot into the roof of Manuel Almunia's net.
That was the first goal Arsenal had conceded in this season's Champions League, but worse was to follow as Sevilla took the lead through Luis Fabiano in the 34th minute.
Moments before, the Brazilian striker had almost capitalised on another Arsenal defensive error, this time by Gilberto, only to be denied by some last-ditch defending.
He made no mistake with his next opportunity though, sending a glancing header from Daniel Alves' free-kick past Almunia's right hand and into the corner of the net.
It was all Sevilla at that point, but Arsenal almost drew level in the 37th minute following a quick breakaway.
Bendtner caused problems in the Sevilla backline and, after the Dane had laid the ball back, Eduardo sent in a shot that was deflected over the bar for a corner with home goalkeeper Andres Palop struggling.
Arsenal might easily have found themselves 3-1 down just before the break, but they were given an unexpected let-off by Kanoute.
He seemed certain to score after Almunia had palmed out a Luis Fabiano shot, but the Mali international screwed his shot wide.
Arsenal started the second half looking in determined mood, and they felt they had good claims for a penalty in the 50th minute when Emmanuel Eboue went down inside the area following a challenge by Christian Poulsen.
That was again rejected by Dutch referee Eric Braamhaar though, leaving Eboue and Bendtner holding their heads in disbelief.
Wenger made his first change of the match in the 55th minute when Cesc Fabregas was replaced by Tomas Rosicky.
Fabregas had been relatively quiet on his return to Spanish soil but he still earned a standing ovation from the home crowd as he left the pitch.
Despite that switch, Sevilla were looking the much more likely scorers and Luis Fabiano went close with a couple of efforts.
Controversy reigned in the 65th minute when referee Braamhaar awarded Sevilla a penalty following what he felt was a handball by Senderos, only to reverse his decision moments later.
The Arsenal players were stunned by the initial ruling, convinced that Senderos had blocked Navas' cross with his chest, and they complained en masse to both the referee and his assistant.
The referee then decided to award a drop-ball instead of the penalty, leaving the home fans fuming.
Sevilla continued to dominate though, and Alves went close in the 77th minute with a speculative 25-yard shot while Keita also fired a shot wide.
The home side then wrapped the match up with three minutes remaining when they were awarded a penalty - with this one standing.
Kanoute went tumbling under the combined challenge of Kolo Toure and Bacary Sagna as he raced to meet a Navas cross, and the Mali international picked himself up to slot home the resulting penalty and settle the outcome.
