Republic of Ireland have fallen to third place in Group D after losing 1-0 to Serbia at the Aviva Stadium.
Aleksandar Kolarov opened the scoring in the early stages of the second half and although Serbia had Nikola Maksimovic sent off, Ireland could not force an equaliser in Dublin.
Serbia now sit five points clear at the top of the World Cup qualifying group, but Ireland are no longer in the runners-up spot after Wales's 2-0 triumph in Moldova.
Ireland needed to try to set the tempo against their talented opponents but Martin O'Neill's side were fortunate not to fall behind after two minutes, with only a timely block from Shane Duffy stopping a goalbound strike from Nemanja Matic.
Slowly but surely, Ireland stamped their authority on the contest and the ball was in the net when Duffy headed past Vladimir Stojkovic, but the Brighton & Hove Albion defender was correctly adjudged to be offside.
Ireland were pressing the play in the final third, but their best chance of the first half came from distance, with Shane Long forcing Stojkovic to tip his strike over the crossbar from 25 yards.
As the game approached the break, Serbia began to dominate and with 12 minutes to go, Darren Randolph needed to be alert to keep out Aleksandar Mitrovic from close range after the Newcastle United forward had met Dusan Tadic's cutback.
Antonio Rukavina also had an opportunity for the visitors but despite being found in time and space around 16 yards from goal, the full-back's first-time effort cleared the bar.
Just 24 seconds after the restart, Serbia should have made the breakthrough but after getting himself free from 20 yards out, Tadic's shot was tame and too close to Randolph.
Ireland were struggling to get anything going and it came as no surprise when Serbia went ahead in the 55th minute as Kolarov rattled a shot into the net via Randolph and the underside of the crossbar.
The goal rocked Ireland and with an equaliser already looking unlikely, the writing appeared to be on the wall until a red card was handed to Maksimovic, who brought down Daryl Murphy as he was about to move in on goal.
It was a lifeline, but Ireland still struggled to create chances against a resolute Serbian backline, although the hosts should have been awarded a penalty with a quarter-of-an-hour remaining when Murphy was pulled back in the area, only for the referee to miss the infringement.
Ireland's biggest opportunity in the closing stages also fell to Murphy but despite making a clean-enough connection with his shot from the edge of the box, Stojkovic got a leg in the way to divert the ball away from danger.
The home supporters were encouraged with five minutes of added-on time, but their team failed to come close to finding the goal which would have left the group wide open with two matches remaining.
Darren Plant
