Singapore were made to rue a late equaliser as they were held to a potentially costly 1-1 draw by Turkmenistan in 2019 AFC Asian Cup qualifying at Jalan Besar Stadium on Tuesday night.
Shakir Hamzah put the Lions ahead after the hour mark with his first international goal. But Altymyrat Annadurdyyyev scored eight minutes from time to rescue a point for the visitors, in front of 3,712 spectators.
The result meant Singapore remain winless in Group E, with two points from three outings, and will most likely need two victories out of their remaining three matches to qualify.
Turkmenistan almost got off to the best possible start by scoring within four minutes of kick off. Myrat Annayev sent captain Arslanmyrat Amanov through on goal, but the latter lashed just wide of the right-hand post from a tight angle.
That stung Singapore into action as they created a half-opportunity six minutes later, with Khairul Amri just failing to connect with Nazrul Nazari's right-wing cross.
Turkmenistan then had a good penalty claim turned down by Japanese referee Yudai Yamamoto on 14 minutes, with Altymyrat Annadurdyyyev seemingly impeded by Singapore goalkeeper Hassan Sunny in the area.
The hosts were largely on top for the remainder of the first half, but were unable to finish off their chances.
First, Safuwan Baharudin flicked his header from Shakir's deep cross just wide of the right-hand post on 26 minutes. Seven minutes later, an innovative short free-kick move involving Zulfahmi Arifin and Faris Ramli resulted in Khairul Amri seeing his deflected shot come off the right-hand post.
Amri, however, had to come off shortly after due to injury and was replaced by Fazrul Nawaz.
From the resulting corner, Hariss Harun connected well with Zulfahmi's inswinging corner, but the header took a bounce off the Jalan Besar turf before going over.
Singapore continued where they left off after the restart, and broke the deadlock three minutes after the hour mark.
After Hariss had won the rebound off his own half-cleared cross, the loose ball fell to Shakir.
The left wing-back brought the ball down with one touch, before thrashing home a superb volley from just inside the box past the helpless Turkmenistan goalkeeper Mammet Orazmuhammedov.
The Lions kept going and should have doubled their advantage on 75 minutes. Safuwan went through on goal via Faris' through ball, but his second touch was too heavy as the ball rolled straight to Orazmuhammedov instead.
They would live to rue that missed opportunity as Turkmenistan found the equaliser seven minutes later.
With the Singapore defence failing to deal with substitute Murat Yakshiyev's inswinging cross, Annadurdyyev stole in to slot past Hassan from eight yards out.
Annadurdyyev could have grabbed the winner three minutes from time after a loose ball fell his way in the area. However, he was unable to keep his resulting on target as the game ended in a 1-1 draw.
Singapore: Hassan Sunny (GK), Irfan Fandi (Faritz Hameed 75'), Daniel Bennett, Zulfahmi Arifin, Nazrul Nazari (Madhu Mohana 69'), Hariss Harun (C), Izzdin Shafiq, Shakir Hamzah, Safuwan Baharudin, Faris Ramli, Khairul Amri (Fazrul Nawaz 36')
Turkmenistan: Mammet Orazmuhammedov (GK), Serdar Annaorazov, Mekan Saparov, Ahmet Atayev, Gurbangeldi Batyrov, Shohrat Soyunov, Arslanmyrat Amanov (C), Myrat Annayev (llya Tamurkin 84'), Umidjan Astanov (Merdan Gurbanov 69'), Ruslan Mingazov, Altymyrat Annadurdyyew