Singapore's two-match unbeaten run in the World Cup Group E qualifiers came to an unlucky end following a 1-0 defeat to Syria in Muscat, Oman, on Thursday.
The Southeast Asian giants started quickly out of their blocks, looking to continue their impressive form that saw them beat Cambodia 4-0 and hold Japan to a goalless draw in Saitama in June.
Bernd Stange's charges outplayed their opponents, but were downed by a lone goal from Ouday Abdul Jaffal in the second period.
In a strange tactical move, Syria resorted to shooting from a distance in the opening minutes. Ouday and Sanharib Malki came up with a slew of ridiculous 30-yard potshots.
The West Asians almost paid the price for underestimating their opponents when Khairul Amri turned and sent a 21st minute shot from way out that sent goalkeeper Ibrahim Alma scrambling to his right.
The Lions had another golden opportunity seven minutes later, when Hafiz Sujad broke the offside trap but saw his shot stopped by Alma's outstretched leg. Amri's follow-up shot was deflected out for a corner as the Syrian defence was once again exposed.
Syria continued to struggle for the rest of the first half, with only Raja Rafe's 34th minute attempt testing Izwan Mahbud.
With two minutes remaining for the break, Omar Khribin's free kick went straight to Izwan, who sent a long punt up the other end and Amri's fierce drive was saved by the Syria keeper who berated his spineless defence.
There was a scare for Bernd Stange when Mahmoud Al Mawas put the ball into the net off Khribin's cut-back from the byline, only for the referee to rule that the ball had gone out of play.
Syria must have had a rollicking at half-time because they came out looking a different team. Ouday stung Izwan's gloves in the 50th minute with a straightforward effort.
Singapore's hard work was undone nine minutes later when Ouday darted his header past Izwan, after some good work down the left flank by Malki.
Amri almost levelled the game at the restart when he turned Hamdi Al Massri before holding his head in disbelief as his shot came back off the post.
Malki had a good chance with 19 minutes remaining, but he glanced his header wide despite being unmarked in the box.
As the visitors pushed forward in search of the equaliser, Syria began to shoot on sight. Another such move saw substitute Abdulrazak Al Husein test the stopper's nerves with a grounder that was palmed out for a corner.
There were huge shouts for a penalty in the 83rd minute when Hafiz was brought down from behind by Ahmad Al Saleh, only for the referee to play the advantage. However, Amri's shot was saved by the Syrian custodian.
Syria are top of the group with six points from their two matches. Singapore have four points from three games, the same as four-time Asian champions Japan, who have a game in hand.
Meanwhile, Malaysia were inflicted a 10-0 Group A World Cup qualifier drubbing at the hands of Asian Cup semifinalists United Arab Emirates in Abu Dhabi on Thursday.
Forwards Ahmed Khalil and Ali Mabkhout went berserk and plundered four (24, 29, 71 and 78 minutes) and three goals (22, 33 and 75 minutes) apiece as Dollah Saleh's side cut a sorry sight yet again after the 6-0 humiliation at the hands of Palestine in June.
It was always just a matter of how many goals Malaysia would concede in the game and at half-time Harimau Malaya found themselves 7-0 down. It was evident that the tally against Palestine at home would be surpassed by the time of the full time whistle.
Defender Mohandad Al Enezi opened the scoring for Mahdi Ali's side in the 16th minute. Habib Fardan Abdullah (25th minute) and Mohamed Ahmed (37th minute) completed the rout.
The UAE are top of Group A with six points from two matches while Malaysia are at the bottom with a point from three games after a home draw against Timor-Leste in June.
Dollah's side will take on UAE's fellow West Asian heavyweights Saudi Arabia at the Shah Alam Stadium on Tuesday while Singapore will host Afghanistan in October.
Singapore: Izwan Mahbud (GK), Shaiful Esah (Shakir Hamzah 85'), Baihakki Khaizan, Madhu Mohana, Nazrul Nazari, Izzdin Shafiq (Khairul Nizam 75'), Hariss Harun (C), Hafiz Sujad, Safuwan Baharudin, Fazrul Nawaz (Faris Ramli 62'), Khairul Amri
Syria: Ibrahim Alma (GK), Ahmad Alsaleh, Hamdi Al Massri, Zahir Alhunaimi, Ahmad Kallasi, Mouajad Alajaan, Omar Khribin, Ouday Abdul Jaffal (Burhan Sahyouni 80'), Sanharib Malki (Omro Al Midani 90+1'), Mahmoud Al Mawas, Raja Rafe (C) (Abdulrazak Al Husein 64')