Singapore's hopes of qualifying for the 2019 AFC Asian Cup went up in smoke after a disappointing 3-0 defeat to Bahrain in front of 2,628 fans at the National Stadium on Tuesday night.
V. Sundramoorthy's men did well to contain the visitors for more than an hour, and looked set to earn a similar result to the 0-0 draw away in Manama eight months ago.
However, three goals in the final 25 minutes saw the Lions extend their winless run to 13 matches. Their last victory came when they beat Camboida 1-0 in a friendly in Nov. 2016.
The result means that they will only have pride to play for in their final Group E game away against Chinese Taipei in March.
In need of the three points, Singapore started off by pressing Bahrain up the pitch and almost scored within a minute of kick off.
Zulfahmi Arifin's free kick was flicked on into the path of Shawal Anuar, but the latter could only slam his volley wide of the left-hand post from a tight angle.
There was another opportunity for the home side six minutes later, with Irfan Fandi stinging the palms of Bahrain goalkeeper Syed Shubbar Ebrahim Alawi with a 30-yard free kick.
The Lions were then forced into an early change, with Shawal replaced by Faritz Hameed on 12 minutes due to injury.
Nonetheless Sundram's men did well to limit the inroads of the Bahraini players, with the visitors needing all of 34 minutes to have their first real opportunity on goal.
Komail Hasan Alaswad found space just outside box to fire a piledriver, but the effort sailed just over the bar.
Singapore could have broken the deadlock just before half-time through a quick break, but Faritz Hameed's cross was a tad too high for Saufwan Baharudin to connect.
Bahrain returned for the second half with much more vigour and should have scored in the 53rd minute. But Abduljabbar's header was somehow denied by Singapore goalkeeper Hassan Sunny from point-blank range.
Singapore then suffered a huge blow just before the hour mark, with centre-back Irfan coming off, replaced by Nazrul Nazuri, due to injury.
His absence was sorely felt as the Lions conceded the opener on 65 minutes.
Mahdi Abduljabbar's initial header was rejected by a stunning Hassan reflex save, but the Bahrain No. 9 reacted the quickest to convert the loose ball.
Khairul Amri then came on to replace Zulfahmi as Singapore's last throw of the dice with 18 minutes left, but the veteran forward found the going tough.
In search of the equaliser, the Lions were hit on the break, conceding a second in the 81st minute.
The Singapore defence fell asleep from a long ball, leaving Jamal Rashed free to fire a confident finish past the onrushing Hassan.
The visitors rubbed salt into wound by scoring a third three minutes later, with Abduljabbar firing home a first-time volley off Abubaker Aadem's flick-on from a corner.
In the other Group E game on Tuesday night, Turkmenistan defeated Chinese Taipei 2-1 at home to remain to secure their qualification along with Bahrain.
Singapore: Hassan Sunny (GK), Irfan Fandi (Nazrul Nazari 58'), Hariss Harun (C), Daniel Bennett, Madhu Mohana, Shahdan Sulaiman, Zulfahmi Arifin (Khairul Amri 73'), Hafiz Sujad, Shawal Anuar (Faritz Hameed 14'), Safuwan Baharudin, Faris Ramli
Bahrain: Syed Shubbar Ebrahim Alawi (GK), Waleed Al Hayam, Sayed Redha Isa Hasan Radhi, Abubaker Aadem, Ahmed Abdulla Ali Abdulla, Sayed Dhiya Shubbar (Hesham Nayem 90'), Abdullah Yaser (Ali Madan 62'), Abdulwahab Ali Alsafi (C), Komail Hasan Alaswad, Jamal Rashed, Madhi Abduljabbar (Sami Alhusaini 84')