The Lions had gone two down in the friendly at the picturesque Sevens Stadium in Dubai, but Shahril Ishak's second half penalty provided a glimmer of hope, before Shahdan Sulaiman's last gasp effort - his first goal in Singapore colours - sealed a commendable comeback.
In their first senior international of the year, Singapore started brightly against European opponents who are coached by German Berti Vogts and who played the likes of Germany and Turkey during their recent, albeit unsuccessful, EURO 2012 qualifying campaign.
However, despite thier initial impetus, Singapore fell behind after only 15 minutes when striker Rauf Aliyev, afforded time and space in the box, fired home past a helpless Hassan Sunny.
A raft of changes at half-time saw Singapore continue to press Azerbaijan, however Radojko Avramovic's men went further behind after 62 minutes, Mahir Sukharov doubling his side's advantage.
Hope sprang eternal for Singapore when Lions captain Shahril converted a penalty on 71 minutes after substitute Qiu Li had been brought down by Agil Nabiyev.
The comeback was complete on the stroke of the full-time whistle when Mustafic Fahrudin's astute pass found LIONSXII midfielder Shahdan who made no mistake with his shot.
"I am delighted to have scored the equalizer so late in the game," Shahdan declared after the game.
"I am glad our tactics paid off and now we can look forward to 2012 having started the year with such a positive result against a European team."
Singapore are now scheduled to face Iraq on Wednesday in their final 2014 World Cup qualifier. Neither team can qualify for the fourth and final stage of qualifying.
Singapore Starting Line-up: Hassan Sunny, Baihakki Khaizan, Shaiful Esah (Irwan Shah 45'), Daniel Bennett, Ruzaini Zainal (Delwinder Singh 80'), Isa Halim (Firdaus Idros 68'), Shahdan Sulaiman, Fazrul Nawaz (Shi Jiayi 45'), Mustafic Fahrudin, Shahril Ishak (Patrick Paranjody 90'), Agu Casmir (Qiu Li 45')