A 3-1 win in the first leg of the 2012 AFF Championship set the stage for a 3-2 aggregate triumph, as the Lions became the first team to win the tournament on four occasions.
More than a decade on, Singapore have since been surpassed by the Thais, who are now seven-time winners of the AFF Championship -- including in four of the last five editions.
In the same time, the Singaporeans have only made it out of the group stage once.
Prior to their latest clash at Singapore's National Stadium on Tuesday evening, the Lions had lost all of their past six encounters with the current kings of the region.
And despite a spirited showing, they were unable to end the unwanted streak as they fell 3-1 in the second round of Asian qualifiers for the 2026 FIFA World Cup -- to a Thailand outfit that just looked to have an extra level of quality.
Never mind that star playmaker Chanathip Songkrasin was absent from the team entirely, or that Teerasil Dangda -- the Thais' main man in attack for the past decade or so -- was only fit to feature off the bench for a maximum of half an hour.
The War Elephants, as they have so often proved, have plenty of other dangerous options.
It took them just five minutes to open the scoring when an intricate passing move paved the way for Supachok Sarachat to lash a powerful effort past Hassan Sunny.
To the hosts' credit, they withstood the early pressure to prevent falling further behind and then started gathering momentum of their own -- culminating in a sweeping foray forward that led to Shawal Anuar bagging the equaliser from close range.
Just when it looked like over a decade of disappointment against Thailand might be about to be a chapter closed for Singapore, the visitors found another level.
Teerasil may only have been available for 30 minutes yet he needed just seconds to have a telling impact, coming off the bench in the 66th minute and immediately releasing Suphanat Mueanta with an exquisite turn and visionary through-pass for his 21-year-old teammate to restore their team's lead.
Then with three minutes remaining, the War Elephants made sure there would be no late drama of a Singapore comeback as Suphanat added his second with a powerful drive from the edge of the box.
For the Thais, it was a much-needed win for their hopes of progressing to the next round of the Asian qualifiers -- especially after they threw away a lead in a 2-1 lose to China PR in their Group C opener.
But for Singapore, their campaign looks over before it has really even begun -- with back-to-back ties next against the Chinese before they take on South Korea, who they lost 5-0 to last Thursday, and Thailand again.
In what was a undeniably tough draw handed to them, progressing to the next stage was always going to be a near-impossible task and -- to Singapore's credit -- they did show plenty of spirit against both the South Koreans and Thailand.
Yet, especially in Tuesday's defeat against regional rivals they would have expected to give more of a run for their money, as opposed to the continental heavyweights that are South Korea, the loss to the War Elephants was another remind that there is still quite a gap that Singaporean football has to make up on if they are to scale greater heights.