Rangers were well beaten by Valencia on Tuesday as Roberto Soldado scored twice in a 3-0 Champions League Group C win.
Tino Costa added a late third for the La Liga side, who climbed above the Gers with the Mestalla Stadium win and, along with leaders Manchester United, are now favourites to emerge from the section and reach the last 16.
With two games to play, Los Che have seven points to United’s ten, with Rangers on five and Bursaspor still on zero.
The Gers had not lost in the group before Tuesday, but will look back on missed chances in Spain, not least Steven Naismith’s tenth minute rattling of the post after he raced forward and had a shot.
Allan McGregor had already denied Juan Manuel Mata’s volley before denying a great effort from the same player, but the Scotland goalkeeper was beaten on 34 minutes.
He flapped at Mata’s corner and the ball bounced off the back of Madjid Bougherra and into the path of Soldado, who rammed home his second goal of the group stages for a half-time lead.
Aritz Aduriz came close to doubling the home side’s lead on 54 minutes but McGregor kept out his powerful header, before a rare Rangers break saw Naismith feed Kenny Miller, but his shot was easy for Cesar Sanchez to hold.
McGregor continued to keep the score down with more stops from Mata and Aduriz, but he was beaten for a second time with 20 minutes to play.
Soldado and Mata played a one-two to press past the Gers defence and the former then shot from an angle. The goalkeeper got a touch, but the ball found the net and Rangers’ hopes looked dashed.
Joaquin was denied by McGregor before Naismith hit the woodwork for the second time with a header on to a forward pass from Bougherra. It bounced off the ground and against the post and with it went any hope of an unlikely comeback for Walter Smith’s men.
Costa then sealed the win in stoppage-time. Miguel pounced on an error from Sasa Papac and crossed for the substitute to slide the ball home via McGregor’s post.