By Gabriel Tan at the Woodlands Stadium
The Rams went ahead in the 14th minute when Moon Soon-ho capitalised on a moment of indecision in the Young Lions defence to score with a rasping drive from the edge of the area.
However, Young Lions came back strongly in the second half and equalised through substitute Nazrul Nazari in the 77th minute, before Faris Ramli poked home the winner three minutes from the end to cap off a stunning comeback from the visitors.
While just three points separated both sides heading into Friday's game, Young Lions were coming off the back of a decent run after picking up ten points from their last six games.
On the other hand, Woodlands had been winless in their last ten in the league after recording victories in their opening two matches, but they got off to a perfect start after 14 minutes.
Hesitant defending from Al-Qaasimy Rahman saw him give away possession to Moon inside his own half, allowing the South Korean to race towards goal before unleashing a terrific strike from the edge of the area that went in off the far post.
Robin Chitrakar's young charges immediately sought to level matters and carved out a good opening in the 21st minute when Sherif El-Masri's freekick from the right was met by a perfectly-timed run from Fazli Ayob, although the 22-year-old was only able to glance a header straight into the arms of Ahmadulhaq Che Omar.
Two minutes later, Sufianto Salleh found space inside the area but blazed his effort over from a tight angle with only the Rams custodian the beat.
Nonetheless, Woodlands remained largely in control of proceedings, with Moon and Hussein Akil causing the visitors a real headache with their constant movement in the attacking third.
Three minutes after the break, Goh Swee Swee carved out a decent opening for himself when he picked up the ball down the right and glided past Al-Qaasimy, before curling in a shot that sailed just over Syazwan Buhari's crossbar.
Eager to inject some pace in his lacklustre attack, Chitrakar introduced Nazrul shortly after the interval and the winger almost made an instant impact when he danced past Duncan Elias down the right, before smashing a shot back off the post.
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Another one of the Young Lions substitutes then came equally close when a slack touch by Farizal Basri inside his own area allowed Haniff Sadique a sniff of goal, although Ahmadulhaq was quick to snuff out the threat with a brave save at the feet of the lanky striker.
However, the pressure the visitors were piling on eventually told 13 minutes from time when Sirina Camara went on a terrific burst down the left, before drilling in a cross that was calmly sidefooted into the back of the net by Nazrul.
Woodlands' problems went from bad to worse in the 80th minute when midfielder Han Yi Guang received his marching orders for a second bookable offence, and the Young Lions made the most of their numerical advantage three minutes from time when they stunningly went ahead after captain Hafiz Abu Sujad stole possession inside the Woodlands area and slipped El-Masri down the left, where the Canadian winger proceeded to slide in an inch-perfect cross for Faris to poke home.
Having seen a much-needed three points all but slip from their grasp, the Rams mustered one final effort to grab a share of the spoils and were extremely unlucky not to do just that at the death when Aloysius Yap fired a shot from the edge of the area that came smashing off the crossbar.
With that, Woodlands were condemned to an 11th consecutive game without a win, while Young Lions ensured they got the second round of the season off to a perfect start.
Woodlands Wellington: Ahmadulhaq Che Omar, Danny Chew, Fabien Lewis, Daniel Hammond, Duncan Elias, Goh Swee Swee (Shamsurin Rahman 69'), Armanizam Dolah, Han Yi Guang, Farizal Basri (Oswind Suriya 85'), Hussein Akil (Aloysius Yap 54'), Moon Soon-ho.
Courts Young Lions: Syazwan Buhari, Faritz Hameed, Sheikh Abdul Hadi, Sirina Camara, Al-Qaasimy Rahman, Faris Ramli, Hafiz Abu Sujad, Aqhari Abdullah (Zulfahmi Arifin 58'), Sherif El-Masri, Fazli Ayob (Haniff Sadique 71'), Sufianto Salleh (Nazrul Nazari 51').