Filip Dordevic condemned Martin O'Neill to a first defeat as Republic of Ireland manager as Serbia came from behind to win in Dublin.
Shane Long had given the home side an eighth-minute lead, but he then passed up two glorious chances either side of James McCarthy's 48th-minute own goal.
Dordevic ultimately won it from close range with 60 minutes gone as the Serbs emerged victorious.
Midfielder Glenn Whelan was handed the captain's armband as the Republic of Ireland faced Serbia at the Aviva Stadium.
Whelan led the side in the absence of Robbie Keane and John O'Shea, and there was a third senior cap for Derby defender Richard Keogh and a start for Norwich playmaker Wes Hoolahan.
Acting Serbia manager Ljubinko Drulovic named skipper Branislav Ivanovic, Aleksandar Kolarov and Nemanja Matic in his starting line-up as he attempted to inflict a first defeat on new Republic boss Martin O'Neill.
Ireland thought they had got off to the perfect start with just two minutes gone as Hoolahan made his presence felt.
His ball out to James McClean allowed the winger to cross to the far post when Whelan sent a volley across keeper Vladimir Stojkovic, with Hoolahan turning the ball home when it looked to be going in anyway.
His joy was halted by an offside flag which went up straight away, but replays suggested midfielder Dusan Basta had played him on.
However, the home side did go ahead six minutes later when striker Shane Long capitalised on Ivanovic's under-hit back-pass to lift a shot over Stojkovic and into the back of the net, his reward for chasing down central defender Marc Wilson's clearance.
Serbia began to work their way back into the game and full-back Stephen Ward had to block Basta's 14th-minute flick from a Lazar Markovic cross with defender Milan Bisevac heading the resulting corner straight at keeper David Forde.
The Millwall stopper was in action once again five minutes later as he got down to claim Markovic's guided effort after Keogh had managed to hold up Dusan Tadic and Filip Djordjevic.
However, Forde needed the help of James McCarthy under the crossbar when Ivanovic powered a header past him from a 21st-minute corner, the midfielder clearing as the Serb skipper argued in vain that his effort had crossed the line.
Long really should have added to his tally on the half-hour after Hoolahan once again performed his role as creator to superb effect.
The Norwich man picked up possession inside his own half and made ground before playing a fine pass into the striker's path as he worked hard to stay onside.
The Hull player ran away from the cover, but gave Stojkovic the chance to block his tame shot, and he was unable to convert the rebound as he fell.
Serbia's defence was under pressure once again two minutes later when full-back Seamus Coleman found himself in an advanced position down the right, and his cross was fortuitously sliced across his won goal by Bisevac.
Kolarov was handed a chance to level seven minutes before the break when he was tripped by Ward 25 yards out, but his free-kick clipped the defensive wall and ran out for a corner.
McClean went much closer at the other end seconds later, but his skidding drive flew just wide, and Forde had to be at his best to claw away Tadic's curling attempt with play switching rapidly from end to end.
Intro: Shane Long's 11th senior international goal handed the Republic of Ireland a deserved half-time lead over Serbia.
The Hull striker made the most of Chelsea defender Branislav Ivanovic's eighth-minute blunder to put the home side ahead, and he should have doubled his tally on the half-hour after being played in by Wes Hoolahan.
However, midfielder James McCarthy prevented Ivanovic from atoning for his earlier error with a goal-line clearance to keep his header out of the top corner.
Ireland's lead evaporated with three minutes of the restart when they were caught out by the invention of the impressive Kolarov.
He played a perfectly-executed one-two with Tadic on the edge of the box and then rolled the ball towards Dordevic.
The covering McCarthy managed to get there first, but he could only bundle the ball into his own net.
But the home side should have been back in front within five minutes when Hoolahan's superb reverse pass split the Serb defence once again to put Long in on goal.
The striker shot early in a bid to catch Stojkovic off his line, but sent his effort wastefully wide.
As the game opened up both sides committed men to attack, leaving space in behind and exposing their respective defences, and Forde had to get down well once again to block Tadic's 58th-minute effort.
But he was beaten once more on the hour when substitute Zoran Tosic's mis-hit shot fell to Dordevic at the back post and he stabbed the ball home.
O'Neill made a series of substitutions in the wake of the goal, withdrawing Hoolahan - to warm applause - McCarthy and Ward as Anthony Pilkington, David Meyler and Ciaran Clark were given a chance to show what they could do.
Tosic could have added his name to the scoresheet with 19 minutes remaining when the ball fell to him six yards out after Dordevic had failed to connect properly with an acrobatic overhead attempt, but his instinctive attempt lacked both direction and pace.
Jon Walters and Daryl Murphy joined the fray as Long and Aiden McGeady departed with Serbia starting to dominate.
The rash of substitutions inevitably interrupted the flow of the game, and although both sides continued to attack, clear-cut chances were few and far between as time ran down.
Kolarov tested Forde from distance at the death, but the keeper was equal to the task once again.