Scotland's hopes of reaching World Cup 2014 were ended by Serbia thanks to Filip Djuricic's double.
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.
|19||F. Đuričić||60' 65'|
|Coach: S. Mihajlović|
for D. Tadić 69'
for L. Fejsa 86'
for Z. Tošić 90+3'
|Southampton overcome Twente, Asoro stars for Sunderland|
|Man City must adapt to Guardiola tactics quickly - Denayer|
|Chelsea and Leicester to play in EFL Trophy as five Premier League clubs refuse|
|Tolisso pulls plug on €37.5m Napoli move to stay at Lyon|
|Ancelotti shrugging off Guardiola´s shadow|
|Uruguay international Lodeiro swaps Boca for Seattle|
|Ibrahimovic will bring United back to where they belong - Larsson|
|Transfer speculation frustrates Aubameyang|
|Willian ready for ´toughest Premier League season in history´|
|Astana 1 Celtic 1: Griffiths hits late equaliser|
|De Laurentiis feels betrayed by Higuain swapping Napoli for Juventus|
|Costa: Chelsea cannot be any worse than last season|
|Wilshere: Xhaka can hold Arsenal midfield together|
|Pato signs four-year deal with Villarreal|
|Higuain sets sights on Champions League after Juventus move|
|Lazio snap up Immobile from Sevilla|
|Batshuayi worth the money, insists Cahill|
|Arnautovic signs new Stoke deal|
|Smith leaves Liverpool for Bournemouth|
|Barcelona insist Arda Turan will stay|
|Andre Gomes: Barcelona suit my identity better than Real Madrid|
|Niersbach to appeal FIFA ban|
|Barcelona agree Mascherano renewal|
|Fernandinho can play in 10 positions - Guardiola|
|Reading´s kit launch is out of this world|
|Ben Arfa: I do not want to be PSG´s star player|
|FA Cup to trial fourth substitute|
|We want Balotelli and he wants us, says Besiktas chief|
|Crowd welcomes Higuain as he arrives for Juventus medical|
|Guardiola warns Man City stars: If you´re not fit, danger is coming|
|Mkhitaryan prepares to prove himself at United|
|Cavani: No pressure replacing Ibrahimovic|
|Wenger vows to keep transfer plans ´secret´ after Lacazette snub|
|Brannagan open to Championship loan move|
|Wenger wants to sign Mertesacker replacement|
|Ancelotti: Bayern´s transfer business done|
|Brisbane Roar sign former Danish international Kristensen|
|Verratti, Luiz missing for PSG|
|Sounders part ways with foundation coach Schmid|
|Mane turned down Manchester United for Liverpool|
|Zidane on Pogba: Until August 31, anything can happen|
|Mkhitaryan driven by father´s death|
|Inter rejected Napoli offer for Icardi, says president|
|Clichy: City fighting fit after Guardiola pizza ban|
|Everton and Burnley win as Hull are held|
|Ajax held by PAOK after Cillessen howler|
|Conte left frustrated by ´crazy´ money in transfer market|
|Neymar makes Barcelona case to Gabriel Jesus|
|Rostov comeback twice for Champions League draw with Anderlecht.|
|Arsenal defender Mertesacker set for lengthy lay-off|
|Conte not selling ´fantastic´ Matic|
|Ibrahimovic keen on MLS and Beckham´s Miami project|
|Neymar: I play for Messi, he´s the man|
|Barcelona reveal details of Andre Gomes deal|
|Suarez bullish over Barcelona prospects|
|Ajax claim Napoli keen on Milik to replace Higuain|
|Totti labels Higuain´s Juventus move ´a disaster´|
|Juventus confirm Higuain deal|
|Pato to Villarreal ´in the final stage´|
|PSG sign Lo Celso|
|Muller: Beating Dortmund will be more fun this season|
|Juventus sign Higuain from Napoli for €90m|
|Pastore: I´m like God in Paris|
|Injured Lanzini out of Olympics|
|Allegri unperturbed by Higuain fee|
|Menezes replaces Bento at Cruzeiro|
|Sporting rejected major bids from Inter and Liverpool for Joao Mario, claims father|
|Pochettino pleased by Tottenham despite Juventus defeat|
|Eriksson: Allardyce the right man for England|
|Mourinho makes United train after stepping off plane from China|
|Hazard can still match Messi, says Pedro|
|Pjanic shows there is life at Juve, with or without Pogba|
|Juventus 2 Tottenham 1: Benatia bags win for Serie A champions|
|Dembele: I am not the Bundesliga´s next superstar|
|Lyon claim €35m Arsenal offer for Lacazette rejected|
|Donnarumma dreaming of Milan captaincy as he eyes long-term stay|
|Robson: Ibrahimovic can match Van Persie´s first year at United|
|Rooney should remain England captain - Eriksson|
|Emery wants new striker at PSG|
|Santos accept Juventus bid for Gabriel|
|Eriksson expects Sweden to try and tempt Ibrahimovic out of retirement|
|Spurs signing Janssen almost quit|
|Leicester stay best for Mahrez - Ranieri|
|Allardyce to take Mourinho cue on Rooney|
|Ings ready to outdo big-money signings|
|Henderson optimistic over Liverpool campaign|
|Allardyce hardened to the challenge of England post|
|Barcelona announce record revenues for 2015-16|
|Moyes enjoys Sunderland win as Palace beat Colchester|
|Stoke complete Allen signing|
|Roma coach Spalletti warns suitors off Manolas|
|Cresswell out for up to four months with knee injury|
|Burnley fan banned by club for racist abuse|
|Dad won´t let me play at the Olympics - Larsson Sr pulls rank|
|Kostic joins Hamburg on five-year deal|
|Tevez: I´d turn down Chelsea and Napoli to stay at Boca|
|Mayoral inspired by Benzema for Wolfsburg stint|
|Allardyce straight into competitive action with England|
|Liverpool, Sevilla fined for Europa League final incidents|
|Barcelona seal Guillemenot signing as part of new Servette deal|
|Niersbach handed one-year ban over World Cup corruption|
|Chelsea and Everton ´still interested´ as Koulibaly eyes Napoli exit|
|´Still working hard´ - Balotelli trains with Liverpool kids|
|Winter breaks, long-ball football and the World Cup: Allardyce in his own words|
|Inter warn Napoli Icardi is not for sale|
|Zanetti wants Simeone back at Inter|
|Stoke snap up Sobhi|
|PSG tougher under Emery - Lucas Moura|
|Totti not ready for retirement - Pallotta|
|Confident Allardyce reveals plan for England success|
|Pochettino to discard three Tottenham players|
|Allardyce: Rooney must wait for captaincy decision|
|Aubameyang: I will only leave Dortmund for Real Madrid|
|Allegri silences questions on Pogba|
|Bruce stands by decision to quit Hull City|
|Pochettino: Not the right time for Argentina job|
|Inter yet to approach De Boer with Mancini exit rumoured|
|Ancelotti trusts me more than Guardiola - Ribery|
|Wijnaldum rejected Everton for Klopp|
|Pre-season Manchester derby cancelled|
|Coutinho excited by ´fast´ Liverpool recruits|
|Cristiano Ronaldo and Conor McGregor step into the ring together|
|Mancini coy on reports linking Icardi to Napoli|
|Nolito reveals why he chose Man City over Barcelona|
|Inter 1 Paris Saint-Germain 3: Icardi absence in defeat fuels Napoli talk|