The dream gig has morphed into a nightmare 11-match winless run, and the national team have slipped to an all-time low of No. 173 in the Fifa world rankings.
But beleaguered Lions coach V. Sundram Moorthy believes he remains the right man for the job.
Ahead of Thursday's international friendly against Lebanon and next Tuesday's Asian Cup qualifier against Bahrain, the 52-year-old told The Straits Times that the Lions are on the right track.
He said before yesterday's training session at Geylang Lorong 12: "We played well against strong teams like Hong Kong and Turkmenistan in recent games.
"We can see the improved performances in the draws and narrow defeats. I believe if we go in this direction, the results will come.
"And when I say they will continue to improve, it also means I have belief (in my coaching philosophy)."
It has not been all smooth sailing for Sundram since he took over from Bernd Stange as the Lions' ringmaster in May last year, before being awarded a two-year extension this March.
There have been some bright sparks, including a defiant 0-0 draw away at Bahrain in March while a switch to a three-man defence inspired better attacking displays in the 1-1 home draws against Hong Kong and Turkmenistan in August and September respectively.
But victories under Sundram have been hard to come by.
In 19 "A" internationals under his charge, Singapore have recorded just a pair of 1-0 wins over Myanmar in his first game and against Cambodia last November, scoring 11 goals and conceding 32 in total.
The Lions were eliminated from the group stages at the Suzuki Cup last November with just a point from three matches, and they have only two points from four Group E qualifiers against Bahrain, Turkmenistan and Chinese Taipei, leaving Sundram winless in all seven competitive matches.
And the man known as the "Dazzler" during the '80s and '90s for his deft dribbles and silky skills is being held responsible for what critics perceive to be dull and defensive football from the Lions.
But if there is a trait he has retained from his playing days, it is his never-say-die spirit.
"From the very first day I signed, there is already pressure to do the job," said Sundram with a laugh.
"International football is totally different from domestic football in terms of intensity and quality of opponents.
"Still, we have competed well against most of our opponents. We played some good teams recently and we were not over-run.
"Results-wise, the Suzuki Cup and the Asian Cup qualifiers have been disappointing but we need to keep working at it, bring through younger players and move forward. Better results will come."
Sundram knows the Lions - bottom of Group E, five points behind second-placed Turkmenistan and with just two qualifiers left - need to beat Bahrain at the National Stadium next Tuesday to even retain an improbable chance of making it to the 2019 Asian Cup.
While they need maximum points, the coach is unlikely to go for an all-out attack formation against opponents they have not beaten in an "A" international before, and who also need a win to be sure of qualification.
He said: "It's the first time we will be playing at the National Stadium this year but national players must love to play at the National Stadium in front of the home crowd.
"And first, we will play a strong Lebanon side, who beat North Korea 5-0 and Hong Kong 2-0 this year, in a friendly to prepare ourselves physically and mentally for Bahrain.
"We need to win, but we have to be smart about how we approach the match tactically.
"It's not a defence-first approach but we have to be tactically disciplined. We had every chance to beat Chinese Taipei and Turkmenistan at home if we had stayed focused.
"We have shown we can compete and match Bahrain away. With the home support, I believe the boys will be motivated and have what it takes to win."