It is a road that has always seen the Lions fall by the wayside, but they will give it another crack when the Asian Cup qualifiers resume in March.
Yesterday, the draw for the third round of qualifiers for the 2019 Asian Cup finals took place in Abu Dhabi, and national caretaker coach V. Sundramoorthy is under no illusions about the task ahead, after being drawn in Group E alongside Bahrain, Turkmenistan and Chinese Taipei.
Singapore have never qualified for the Asian Cup finals, apart from getting an automatic slot as hosts in 1984.
"We have been drawn against good teams. At this stage, we are aware that there are no easy games and we will prepare ourselves accordingly," Sundram said.
"We are looking forward to the first match on March 28 (away to Bahrain) and will try our best to qualify for the 2019 AFC (Asian Football Confederation) Asian Cup in the United Arab Emirates."
With the Lions set to play in Bahrain in two months, it will mark a return to action since November's poor outing at the Asean Football Federation (AFF) Suzuki Cup, the regional tournament which saw the Lions finishing bottom of their group with no wins, one draw and two defeats.
LIONS' GROUP E FIXTURES
March 28: vs Bahrain (away)
June 13: vs Chinese Taipei (home)
Sept 5: vs Turkmenistan (home)
Oct 10: vs Turkmenistan (away)
Nov 14: vs Bahrain (home)
March 27, 2018: vs Chinese Taipei (away)
That stretch of poor form saw Singapore slide down to 165th in Fifa's world rankings, a yardstick that was used yesterday in determining the mechanics of the draw.
As one of the lowest-ranked teams, the Lions - 32nd in Asia - were in Pot Four, the last bowl.
Although right-back Faritz Hameed felt that the Lions have a tough assignment ahead, it is by no means Mission Impossible.
"This is the third round of the qualifiers and surely, we will meet the strong teams. We have to go into this with confidence," said the 27-year-old Geylang player.
"We have some experience playing against Bahrain and they are a typical Middle East team - strong and fast. But it is up to us to give a tough fight and play to the best of our capabilities."
Singapore have recent experience playing against the Bahrainis, who are ranked 123rd in the world.
Last September, the Lions lost 1-3 away in a sparring match in the city of Riffa. In 2014, the national team then led by Bernd Stange, were defeated 2-0 in another friendly.
The Lions have played 143rd-ranked Turkmenistan only once, in Ho Chih Minh City in 2009, when they won 4-2.
The last time Singapore met Chinese Taipei (world No. 157) was a 3-2 friendly win at the Jalan Besar Stadium in 2011. Their other meetings were three Merdeka Cup matches from 1966 to 1968 and an Asian Games encounter in 1966.
The Lions reached the third round of the Asian Cup qualifiers after finishing third in the second round of the 2018 World Cup qualifiers, which also served as a qualifier for the continental tournament.
Powerhouses such as Iran, Japan, South Korea, Australia, Uzbekistan and Qatar are among 12 nations already qualified for the finals, which will be hosted by the United Arab Emirates.
Then, Singapore was third in the round-robin group behind winners Japan and Syria, and ahead of Afghanistan and Cambodia.
Yesterday's draw saw 24 teams split into six groups of four nations. The top two teams will advance, joining the 12 already-qualified nations at the 24-team finals.
Sundram told The Straits Times that he will be arranging friendlies ahead of the qualifiers, with the intention of finding sparring partners that play a similar style of football as their upcoming opponents.
And with the AFF Cup flop still fresh in their minds, the former national striker has asked for fans and the media to rally behind the Lions.
He said: "Please give the national team the support."