A first international goal from Irfan Fandi was not enough for Singapore at Kopetdag Stadium in Ashgabat on Tuesday night as they fell to a late 2-1 defeat to Turkmenistan.
The Lions seemed on course for a heroic away draw before suffering a 93rd-minute sucker punch when the home side scored their winning goal.
Earlier, the eldest son of Singapore legendary forward Fandi Ahmad equalised for Singapore on 27 minutes to cancel Vahyt Orazsahedov's 18th-minute opener.
Continuing in the 3-4-3 formation devised by coach V Sundramoorthy, the Lions put up a creditable display, and it looked like Irfan's goal was enough to earn them a second consecutive draw in competitive matches away from home.
However, the hosts would break the Singaporeans' hearts three minutes into injury time. Orazsahedov popped up with his second of the night to send the home fans wild.
In Tuesday night's other Group E game, Chinese Taipei also scored late to defeat Bahrain 2-1 at home.
Those results meant Singapore's qualifying hopes are all but over.
Stranded at the bottom with just two points from four outings, they need to win their final two games against Bahrain at home and vs Chinese Taipei away and hope other results go their way to stand a chance of progressing from Group E.
Turkmenistan: Mammet Orazmuhammedov (GK), Mekan Saparov, Ahmet Atayev, Gurbangeldi Batyrov (Serdar Geldiyev 77'), Shohrat Soyunov, Arslanmyrat Amanov (C), Myrat Annayev (Murat Yakshiyev 56'), Umidjan Astanov (Merdan Gurbanov 66'), Bahtiyar Hojaaahmedov, Altymyrat Annadurdyyew, Vahyt Orazsahedov
Singapore: Hassan Sunny (GK), Irfan Fandi, Daniel Bennett, Hariss Harun, Madhu Mohana, Izzdin Shafiq, Shahdan Sulaiman, Hafiz Sujad, Safuwan Baharudin, Faris Ramli (Ikhsan Fandi 87'), Fazrul Nawaz (Yasir Hanapi 77')