However, there was a silver lining for Walter Smith's side as Lyon could only draw 2-2 at home to Barcelona. That means the Gers will qualify for the round of 16 if they can avoid defeat to the French side at Ibrox on December 12.

At the Gottlieb-Daimler Stadion, the Gers took the lead through substitute Charlie Adam's opener on 27 minutes, which was cancelled out by Cacau on the stroke of half-time.

It was then the hosts' turn to take the lead when Pavel Pardo's low drive on 62 found its way past goalkeeper Allan McGregor - but Barry Ferguson calmly placed an equaliser into the back of the net eight minutes later.

The visitors looked set to earn a hard-fought point - but their hearts were broken five minutes from time when Marica cheekily flicked an effort past McGregor to give Stuttgart their first win of the group campaign.

Rangers had started the game well, with DaMarcus Beasley scuffing a shot at keeper Raphael Schafer and David Weir having a goalbound header hacked off the line by Ludovic Magnin.

Lee McCulloch had to be replaced by Adam, whose first touch ended in the back of the net after he bundled in Carlos Cuellar's header from a corner.

Cacau drew the hosts level on 45 though, backheeling a shot from Thomas Hitzlsperger into the net.

Smith's woes were doubled on 62 when Pardo made it 2-1 - but sub Steven Naismith set up a leveller, intercepting a throw-out by Schafer and then crossing for Ferguson to keep his cool and sidefoot the ball home.

Marica then latched on to Magnin's late cross - and it means Rangers must not be beaten by Lyon to ensure qualification to the knockout stages.