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Liverpool’s Champions League hopes are hanging by a thread after they were denied a famous victory in Lyons by a last-minute equaliser.

It had looked as though Ryan Babel’s late wonder-goal had thrown Liverpool and manager Rafael Benitez a Champions League lifeline in France. The Dutchman, a second-half substitute for Andriy Voronin, let fly with a 25-yard shot which flew into the top corner with just seven minutes left. But Lisandro Lopez broke the visitors' hearts when he poked home an equaliser just 30 seconds from the end of normal time.

With two more matches left in Group E, Liverpool are five points adrift of Fiorentina in second place and their hopes of further progress is out of their own hands following the Italian side’s 5-2 drubbing of Hungarian side Debrecen.

Fiorentina can ensure the Merseysiders' elimination with victory over Lyons in their home game on Matchday 5 on November 23.

Benitez’s side only had themselves to blame for failing to secure the victory they craved, as they created the clearer chances in the first half in particular without being able to find the crucial goal.

Fernando Torres, starting despite his much-publicised hernia injury, wasted a glorious early chance to give Liverpool the lead. The Spain striker found space in the penalty area from Emiliano Insua's left-wing cross but saw his shot saved by the legs of Hugo Lloris, the goalkeeper.

The visitors were on the back foot in the early stages and Jose Reina was forced to make a save from a long-range drive by Michel Bastos.

But Liverpool, despite their injury problems, carried the greater threat and another cross from Insua fell at the feet of DIrk Kuyt after being miscontrolled by Yossi Benayoun. The Dutchman's strike was well hit, but Lloris reacted superbly to tip the ball over the crossbar. Andriy Voronin then got clean through but his low drive was kept out by the left leg of Lloris.

Arguably the best chance of the night fell to Lucas Leiva midway through the second half. The Brazilian found himself clear inside the left edge of the area, but Lloris snaked out his left hand to make a superb save and Torres’s follow-up overhead kick was cleared off the line by Aly Cissokho.

Arsenal failed to join Manchester United and Chelsea in the knockout stages despite crushing Dutch side AZ Alkmaar 4-1 at the Emirates Stadium. Arsene Wenger’s side were in magnificent form, but were made to wait for their place in the last 16 because of Standard Liege’s victory over Olympiakos.

Arsenal grabbed a 25th-minute lead courtesy of a gift from the visitors. Cesc Fabregas cut inside and beat goalkeeper Sergio Romero at his near post with a tame shot from the edge of the penalty area.