The much-maligned Ryan Babel scored a wonderful goal with just seven minutes left and if Liverpool could have hung on to that lead it would still have had a realistic chance of reaching the last 16.

But when Lisandro Lopez struck an equaliser in the final seconds for Lyon, Liverpool knew its own hopes were left hanging by a thread.

Fiorentina's 5-2 win over Debrecen keeps them firmly in second spot in Group E and Liverpool will need a miracle after this devastating blow.

In Florence, goals from Adrian Mutu and Gergely Rudolf saw the sides all square at half-time but Dario Dainelli, Riccardo Montolivo and Marco Marchionni all struck between the 52nd and 61st minutes to take the game away from Debrecen.

Adamo Coulibaly pulled one back before Alberto Gilardino netted the final goal of a frantic second half.

Two goals in the last five minutes spared Jose Mourinho's blushes at Dynamo Kiev and reignited Inter Milan's campaign in Group F with a 2-1 win.

Andrey Shevchenko, a legend at Inter's city rivals AC Milan, scored the only goal of the first half after 21 minutes, but Inter piled on the pressure in the second period and it paid off as the in-form Diego Milito equalised in the 86th minute and Wesley Sneijder won it a minute from time.

Even a draw would have kept the Italians bottom of Group F, but as it was they went top - a point ahead of Rubin Kazan and Barcelona, who played out a 0-0 draw earlier in the night.

Sevilla booked its spot in the last 16 by holding on for a 1-1 draw against battling Stuttgart at the Ramon Sanchez-Pizjuan.

Winger Jesus Navas put Sevilla ahead in the 14th minute but the visitors staged a second-half fightback and deservedly claimed a point thanks to Zdravko Kuzmanovic's deflected 25-yard strike 12 minutes from time.

Rangers' hopes were left in the balance when a late equaliser from Unirea Urziceni denied them a first victory in the tournament this season.

Lee McCulloch thought he had secured the win with a superb strike with just 11 minutes to go but Unirea hit back to claim a 1-1 draw when substitute Marius Onofras grabbed a last-gasp leveller.

Arsenal all but secured its place in the last 16 after taking apart AZ Alkmaar 4-1 at Emirates Stadium.

Standard Liege's 2-0 win over Olympiacos means, mathematically, Arsene Wenger's side could yet be overtaken for the top two places in Group H.

Arsenal, who is now unbeaten in 12 games, was always in control, Cesc Fabregas setting the Gunners on their way after 25 minutes, before Samir Nasri made it 2-0 on the stroke of half-time with Fabregas again and then Abou Diaby putting the result beyond doubt.

Jeremain Lens netted a consolation for the visitors, who now face a battle to finish third and go into the Europa League.

In Belgium, goals in either half from Dieudonne Mbokani and Milan Jovanovic earned the home side their first win in Group H and moved them two points behind their second-placed opponents in the standings.