Singapore continued their winless run in 2017 after a narrow 1-0 loss to Lebanon in a friendly at the National Stadium on Thursday night.
An early goal by Lebanon stand-in captain Ali Hamam was enough to separate the two sides in front of a sparse home crowd.
The defeat meant V Sundramoorthy's men have failed to win their last 12 matches since beating Cambodia in November 2016.
The game was meant as a tune-up for the Lions to their do-or-die 2019 Asian Cup qualifier against Bahrain at the same venue next Tuesday.
They will need to win their final two Group E games and hope for other results to go their way to qualify for the continental tournament for the first time since being hosts in 1984.
Singapore had actually started off in promising fashion, with Shawal Anuar earning a couple of set pieces, but the Lebanon defence coped well on both occasions.
The Lions went agonisingly close to breaking the deadlock on 10 minutes, but Safuwan Baharudin -- deployed as a forward -- was inches off from connecting with Faris Ramli's teasing left-wing cross.
Lebanon gradually settled into the game and sounded a warning in the 15th minute, with Hamam heading Ahmad Jalloul's free kick straight at Hassan Sunny.
However, the home side failed to heed that and conceded the opener just three minutes later.
Right-back Hamam was allowed acres of space to sneak into the Singapore box, before firing home a neat left-footed finish beyond Hassan's reach.
Singapore toiled hard and could have equalised on 38 minutes, but Safuwan drilled wide of the left-hand post with just Mehdi Kahlil to beat after being teed up by Shawal.
At the other end, Hassan had to be alert to keep out a couple of close-range drives by Rabin Ataya and Kaseem El Zein to ensure the score line stayed intact till half-time.
The Singapore custodian carried where he left off seven minutes into the second half by denying a goal-bound Nader Matar volley with his legs.
Aided by a number of substitutions, the home side began to play better and came close again on 65 minutes.
Safuwan's left-wing cross was half-cleared into the path of Shahdan Sulaiman on the edge of the box, but the latter's resulting piledriver flew inches over the bar.
Sundram then threw on experienced forward Khairul Amri late on, but the Lions found it hard to breach the stout Lebanese defence.
The visitors could have doubled their advantage on 79 minutes when Hafiz Sujad made a hash of his attempted clearance on Maher Sabra's left-wing cross, but substitute Mohamad Tahan could only fire into the side netting from six yards out.
Time soon ran out for the Lions, who will have one last chance five days later to avoid going the entire year winless.