Liverpool’s chances of progressing in the Champions League took a big hit when the five-time European champions conceded late to draw 1-1 at Lyon, which advanced to the next round.
Liverpool looked to have secured victory when substitute Ryan Babel scored with seven minutes left but Lisandro took advantage of a defensive error to equalise in the last minute and put the French team through.
With Arsenal moving to the verge of qualification with a 4-1 win over AZ Alkmaar, Liverpool is in severe danger of becoming the first English club to fall at the group stage since Manchester United in 2005.
Even wins in its final two games may not be enough.
Sevilla advanced to the knockout stage after its 1-1 draw at Stuttgart and Inter Milan scored twice in the last four minutes to revitalise its chances with a 2-1 win at Dynamo Kiev.
But Liverpool let its winning position slip when defender Sotiris Kyrgiakos tumbled to the ground while contesting a long ball into the area, allowing Lisandro to steady himself and shoot past goalkeeper Pepe Reina.
“We deserved to win,” manager Rafa Benitez said. “To concede a goal in the last minute is really unlucky. I will see the replay and analyse carefully.”
Goalkeeper Hugo Lloris had starred for Lyon, which won 2-1 at Anfield two weeks ago. Lloris saved from Lucas Leiva in the 69th and then helped block Dirk Kuyt’s overhead kick on the rebound.
But Liverpool remained shaky in defence and remained under pressure even after Babel had smashed a shot past Lloris from well outside the area.
Liverpool has just four points from four games, six fewer than Lyon and five fewer than Fiorentina, which routed Debrecen 5-2 through goals by Adrian Mutu, Dario Dainelli, Riccardo Montolivo, Marco Marchionni and Alberto Gilardino.
“It’s hit us hard,” Liverpool defender Jamie Carragher said. “A draw doesn’t mean we were totally out of it but a win would have been great.”
Arsenal needs just one more point to be sure of following Manchester United and Chelsea, which advanced Tuesday alongside FC Porto and Bordeaux on Tuesday, into the next round with a third win from four games.
Cesc Fabregas put the Gunners ahead at Emirates Stadium in the 25th with a soft 20-metre (yard) shot that goalkeeper Sergio Romero let in at the near post and Samir Nasri made it 2-0 just before halftime, stepping inside a defender and placing a shot in at the post from the edge of the area.
The Dutch side conceded again in the 52nd, giving the ball away in its own half and letting Andrei Arshavin set up Fabregas for a shot into the top corner.
Abou Diaby made it 4-0 in the 72nd from Arshavin’s back-heeled pass.
“Let’s keep this attitude and spirit and we can deliver something special,” Arsenal manager Arsene Wenger said. “They have a fantastic attitude and great quality and great spirit.”
Standard Liege kept alive its faint hopes of securing runner-up spot to Arsenal in Group H with a 2-0 win over second-place Olympiakos.
Arsenal has 10 points, four more than Olympiakos and six more than Standard. Even AZ still has a chance of progressing despite being stranded in last place on two points.
Sevilla advanced despite surrendering a late goal to draw 1-1 against Stuttgart.
Sevilla had mostly backed off after Jesus Navas opened the scoring in the 14th minute at the Ramon Sanchez Pizjuan Stadium and Zdravko Kuzmanovic equalised with a powerful shot into the top of goal.
Sevilla dropped its first points in Group G but stayed top with 10 points, while Stuttgart has three. Unirea Urziceni drew 1-1 with Rangers to move to five points, three more than the Scottish club.
Inter Milan vaulted from last to first place in Group F, ahead of Barcelona.
Diego Milito equalised in the 86th after Andriy Shevchenko had given Dynamo Kiev the lead midway through the first half and Wesley Sneijder pounced on a goalkeeping error to hit the winning goal in the 89th.
Inter has six points in the competition’s tightest group, one more than Rubin and Barca, and two more than Dynamo Kiev.