Before the match, the statistics made for unpleasant reading: Three years since a last competitive win (beating Cambodia 2-1 in a World Cup qualifier), and four years since a win in the Asean Football Federation (AFF) Suzuki Cup.
That drought finally ended last night when Singapore defeated Indonesia 1-0 to begin this edition of the biennial regional tournament with three points.
Hariss Harun delivered the winning goal, a fierce right-footed drive into the net in the 37th minute after a right-wing cross from Gabriel Quak was not cleared.
Coincidentally, Hariss was also on the scoresheet the last time Singapore won in the AFF Cup, netting a brace in a 4-2 win over Myanmar at Kallang in 2014.
Singapore football's slump is well-documented. From a raft of poor results in age-group competitions to the senior team losing their mojo.
But interim national coach Fandi Ahmad pragmatically tried to raise his fallen troops with perceptive man-management and effective tactics.
The Lions responded with an energetic and committed 90-minute performance in front of 30,783 fans at the National Stadium, earning them rousing applause that had not been heard for a few years.
There could have been more goals for Singapore but Yasir Hanapi's ninth-minute shot was parried away and Faris Ramli's 51st-minute lob bounced off the bar.
In the end, Hariss' goal proved to be enough to seal the three points for this opening Group B game.
"It's been so long since we had seen such a good atmosphere," noted Fandi.
"We are delighted the fans came down. These three points are very crucial and what a relief for Singapore football."
Indonesia coach Bima Sakti complimented the Lions, saying: "The Singapore team have good organisation and good transition from defence to attack. That created big problems for us."
What arguably swung the game for Singapore, and won over the Kallang crowd, was the sheer hard work the Lions put in, evident by the intense pressing and tracking back.
Fandi said: "We did our job very, very well.
"We know Indonesia's wingers are fast, so we had to close them down. Beto (striker Alberto Goncalves) is a good striker but today, he had no supply.
"I'm just very happy for our boys, we are very solid and they really deserved this win."
In the other Group B game, striker Adisak Kraisorn scored six goals as defending champions Thailand thrashed Timor-Leste 7-0.
Adisak's haul was one short of the tournament record for a single match. That mark is held by former Singapore striker Noh Alam Shah, who netted seven in an 11-0 rout of Laos in 2007 and is now player-mentor with the Lions.