In the first of two friendlies against their India counterparts in the build up to the next month's Southeast Asian (SEA) Games, the Singapore Under-23 fell to a narrow 1-0 loss at Choa Chu Kang Stadium on Sunday night.
Richard Tardy's side had put up a resilient defensive display, but the hard work was undone by a late Germanpreet Singh strike.
The Young Lions put out a strong starting eleven, with brothers Irfan and Ikhsan Fandi -- sons of Singapore legend Fandi Ahmad -- starting in defence and attack respectively.
Irfan was busy at the back, sweeping away the danger from the electric Indian attacks, while Ikhsan made a nuisance of himself up front.
The latter showed some great footwork on the left byline midway through the first half, but had his resulting shot blocked for a corner.
The visitors, coached by Englishman Stephan Constantine, were more composed in possession and should have gone ahead on 29 minutes.
Left winger Nanda Kumar latched onto a long ball into the box, but saw his volley swerve just wide of the right-hand post.
Singapore also went close just before the break. Ikhsan's ambitious volley from Syahrul Sazali's long ball was well held by India custodian Vishal Kaith.
Tardy's Lions continued to create good openings in the second half, but were let down by a lack of a final product.
India started to find more inroads after the hour mark, with Lallianzuala Chhangte's 63rd-minute effort ruled out for offside.
Nonetheless, Constantine's charges kept pushing forward and got their reward in the 80th minute.
A poor clearance from Irfan fell to Germanpreet inside the area and the latter needed no second invitation to lash a raking effort beyond Singapore goalkeeper Zharfan Rohaizad.
The home side did create an opportunity four minutes before the end to equalise, but Ikhsan's close-range shot went straight to Kaith.
The final whistle soon sounded to signal a win for the India U23s. But the Singaporeans will have a chance to avenge this defeat when they meet again on Wednesday night.
"I am not happy, you can see faces of the players... they're disappointed because the target was to perform very well and get positive result," Tardy said.
"Today I can't say something about spirit of players but we lost 1-0 today, we don't score. We want to push and press but we made a mistake unfortunately, but Irfan [whose error it was] saved us many times. But we can keep confidence because, don't forget, India is a good physical team."
Singapore Under-23: Zharfan Rohaizad (GK), Darren Teh (Rusyaidi Salime 64'), Irfan Fandi, Shahrin Saberin (C) (Lionel Tan 46'), Syahrul Sazali (Jordan Chan 81'), Amiruldin Asraf (Faizal Roslan 71'), Muhelmy Suhaimi (Amirul Adli 89'), Adam Swandi, Taufik Suparno, Hanafi Akbar, Ikhsan Fandi
India Under-23: Vishal Kaith (GK), Nishu Kumar (Davinder Singh 77'), Lalrutthara (C) (Sarthak Golui 73'), Ranjan Singh, Germanpreet Singh, Nikhil Chandrashekhar (Lallianzuala Chhangte 46'), Manvir Singh (Hitesh Sharma 71'), Lalhlimpuia Daniel (Alen Deory 82'), Nanda Kumar, Jerry Lalrinzuala, Anirudh Thapa (Robinson Singh 71')