Shawal Anuar scored his first international goal but it was not enough to prevent Singapore from falling to a 2-1 friendly defeat to Afghanistan in Doha on Thursday night.
After Sharif Mukhammad had handed Afghanistan a fifth-minute lead at the Al Sailiya Sports Complex, Shawal got the Lions back in the contest with a clinical strike immediately after the restart.
But Mustafa Azadzoy capitalised on some sloppy defensive play to help the Afghans score the winner in the 57th minute.
In what was V. Sundramoorthy's first game in charge since being handed a two-year extension as Singapore coach, there was certainly no shortage of motivation with the 2019 AFC Asian Cup qualifier against Bahrain coming up on March 28.
With that game in mind, Sundram opted to name an experienced starting lineup, boasting the likes of Hariss Harun, Hassan Sunny and Khairul Amri, although there was also room for up-and-coming prospects in the form of Shawal and Irfan Fandi.
Nonetheless, with just five minutes on the clock, it was Afghanistan took the lead when a cross from the left was half-cleared only as far as to Mukhammad.
Finding himself with time and space, the 27-year-old instinctively fired away a snapshot on the volley and made no mistake in sending it past Hassan.
To their credit, the Lions did look to issue a response immediately, despite some testing conditions in Doha, with gusty winds adding to the challenge for the players.
They did threaten on a couple of occasions. But both times, Yasir Hanapi and Amri were just unable to connect with decent deliveries from the left by Faris Ramli and Shakir Hamzah.
Likewise, Afghanistan also did show one or two positive signs, with playmaker Faysal Shayesteh looking to run the show for them, although they failed to really trouble Hassan again.
But less than a minute after half-time, Singapore found themselves level, courtesy of a fine effort by Shawal in only his second cap.
There appeared to be little danger when Hariss received possession just inside the opposition half. But, with the help of the wind, his searching ball out wide to Shawal ended up taking his teammate much closer to goal.
Despite being faced with an acute angle, the Geylang International man showed why Sundram has been keen to put his faith him, rifling a left-footed shot into the bottom corner.
Singapore were certainly showing a lot more energy and desire than they did in the opening 45 minutes. But just when it looked like the momentum was swinging in their favour, they found themselves behind again.
Having just regained possession and looking to counter, the Lions immediately lost it back inside their own territory. Leading the breakaway for the Afghans was Kanischka Taher, who charged to the edge of the box before slipping a lovely pass for Popalzay to run onto and lash home.
From then on, the worsening conditions were always going to make it difficult for Singapore to peg their opponents back once again. As the game entered its closing stages, Afghanistan looked more than happy to sit back and consolidate the result. It was from set pieces where the Lions looked particularly dangerous, with both Khairul Nizam and Safuwan Baharudin having opportunities but failing to hit the target with headers.
Then, in the final minute, it looked as though they would force the draw when Nizam found himself through on goal. Having made a fine start to 2017 at club level, he seemed destined to equalise as he fired away a firm effort, only for Ovays Azizi to make a smart save and secure the triumph for Afghanistan.
Singapore: Hassan Sunny, Faritz Hameed, Safuwan Baharudin, Irfan Fandi (Daniel Bennett 78'), Shakir Hamzah, Izzdin Shafiq (Fahrudin Mustafic 80'), Hariss Harun, Yasir Hanapi (M. Anumanthan 82'), Shawal Anuar (Safirul Sulaiman 67'), Faris Ramli (Juma'at Jantan 46'), Khairul Amri (Khairul Nizam 63')