A quickfire second-half double strike from Heerenveen forward Filip Djuricic brings to an end any chances that Gordon Strachan's men had of reaching Brazil in 2014
Two defensive errors from Alan Hutton allowed the Heerenveen forward to score twice in five second-half minutes, leaving Gordon Strachan’s side bottom of Qualifcation Group A with just two points from six games.
Both sides tasted defeat to regional rivals in their last game and each manager decided to make six changes to their teams, with Gordon Strachan handing debuts to Liam Bridcutt and George Boyd.
Serbia were in on goal inside a minute, a ball over the top falling to Duricic, who was charged down by goalkeeper David Marshall.
Marshall then fumbled a shot from Dusan Basta after nine minutes but he recovered in time to collect the ball.
Basta was involved again four minutes later, crossing for skipper Branislav Ivanovic, who headed weakly past the post.
Marshall was called into action again when Djuricic received a long ball from Matija Nastasic, running into the box before rolling a shot to the goalkeeper's left, though pressure from Grant Hanley meant that the effort was a weak one and the Cardiff City man was able to save easily.
Zoran Tosic then pulled a shot across Marshall's goal from inside the area, his left-footed attempt bouncing wide of the far post.
Clever play from Steven Whittaker had Boyd inside the six-yard box but his pass back across the goal was blocked by a defender with Scotland starting to enjoy a bit more possession going forward.
The visitors started the second half much more brightly and had the ball in the back of the net shortly after the restart, Steven Naismith sweeping the ball into the net from 16 yards from a pass from substitute Charlie Adam - but the Everton forward was correctly ruled offside.
A good passing interchange between Ljubomir Fejsa and Tosic saw the former send in a raking strike from 20 yards out that Crawford had to get down to save.
Jordan Rhodes should have put Scotland ahead after an hour, charging down a weak pass in the Serbia back line before hitting a poor shot right at Vladimir Stojkovic from just inside the box.
Serbia punished Scotland for that miss seconds later, charging up the park before Tosic, who had been lost completely by Hutton, played a pass into Fejsa. He was tackled in the box and Djuricic collected the ball four yards out, coolly turning to face the goal and slamming the ball past a helpless Marshall.
Another Hutton error gave Serbia their second goal five minutes later, losing the ball to Nenad Tomovic, who played in Djuricic for his second.
Serbia almost added a third in the second minute of stoppage time as Ivanovic dragged a long-range effort just past the post after Basta played the captain in following a bursting run.