Singapore have not reached the semifinals of the AFF Suzuki Cup since they last won the tournament in 2012.
Although they have only played once so far in the ongoing edition -- Sunday's 3-0 win over Myanmar -- the Lions know a second consecutive victory in Group A against Philippines on Wednesday would put them tantalisingly close to reaching the last four already.
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With record five-time champions Thailand overwhelming favourites to top the group, although they were not at their best as they opened their campaign by beating Timor-Leste 2-0 at the weekend, the second semi berth was originally expected to be contested between hosts Singapore, Philippines and Myanmar.
Given Myanmar have had a troubled lead-up to the campaign both on and off the field, and were comprehensively beaten in their opening match, that three-horse race now looks an outright duel between Singapore and Philippines.
Which makes Wednesday's tie all the more crucial -- and tantalising.
Victory -- and six points from two matches with another three expected against minnows Timor-Leste -- would almost make it certain that Singapore could afford to lose to the Thais in their final game and still advance.
The Lions have good reason to be confident in their chances after Sunday's display, with two-goal hero Ikhsan Fandi the standout performer, while others like captain Hariss Harun, tournament debutant Song Ui-young and star defender Safuwan Baharudin all impressing.
But there were also areas for improvement with Singapore easing up in the second half against Myanmar, which allowed their opponents to threaten to force their way back into the contest.
Given Thailand are the one side in the five-time group not in action on Wednesday, victory for Singapore would also see them move clear at the top of the table and put the pressure on the Thais ahead of their own meeting with Philippines on Dec. 14.
When asked by ESPN about the potential significance of the game despite the competition still being in its early stages, Singapore coach Tatsuma Yoshida said: "Winning the first match was a very important three points for us. Normally, you would think it would be us, Philippines and Myanmar aiming for that second position because Thailand are still of a different quality.
"We always aim for the top. We want to be challengers and reach the semifinals or even the final, but we must always be aware that Philippines are a side with good quality."
The Azkals certainly boast talented individuals, especially in recently-naturalised Spanish-born striker Bienvenido Maranon and captain Stephan Schrock.
They also boast Suzuki Cup pedigree having reached the semis in four of the past five editions, a feat that puts them on equal footing with the likes of Thailand, Vietnam and Malaysia.
Yet, Philippines have not had the most ideal of build-ups to the tournament with Schrock only joining up with the side in recent days, while coach Stewart Hall confirmed on Tuesday that centre-back Jefferson Tabinas -- based in Japan with second-tier outfit Mito Hollyhock -- has officially been ruled out.
It leaves the prowling Lions in prime position to claim a second consecutive win of their campaign.
One that could just prove pivotal in them advancing into the semifinals for the first time in almost a decade.