Bernd Stange's final match as Singapore coach was an unhappy one as Singapore were beaten 2-1 by Afghanistan in their final 2018 AFC World Cup Group E qualifier.
Khaibar Amani put the Afghans ahead at the neutral venue of the Takhti Stadium in Tehran before Josef Shirdel struck to seal the win for them. Singapore got a late consolation through Fazrul Nawaz but could not muster an equaliser to give their departing manager a fond farewell.
Despite the loss, the Lions are still through to the third round of qualifying for the 2019 AFC Asian Cup, with third spot in Group E, already wrapped up after Afghanistan's 5-0 defeat at the hands of Japan last week.
Meanwhile, there is also a chance the Afghans could automatically advance with the victory, although they will have to wait for other results to find out if they finish as one of the four best fourth-placed teams across the region.
But they certainly held up their end of the bargain, showing plenty of endeavour from the opening whistle to take the game to their opponents.
Hassan Amin had the first real chance of the game in the 11th minute when he broke free inside the box after a poor clearance by Zulfahmi Arifin, but was denied by Hassan Sunny, before Kanischka Taher threatened with a free-kick seven minutes later that flashed past the near post.
Nonetheless, they duly broke the deadlock six minutes after the half-hour mark when Zubayr Amiri's left-wing cross was nodded by Lions defender Afiq Yunos into the path of Amani, who made no mistake at the far post.
Buoyed at taking the lead, Afghanistan continued to enjoyed the better of proceedings but Hassan did well with a flying save to keep out Taher's long-range drive nine minutes into the second half, before Omid Popalzay spurned a good opportunity when he sent a lob over in a one-on-one with the Singapore keeper.
With 11 minutes remaining, the Afghans finally doubled their lead when Taher played a first-time pass from a high ball to Shirdel, who reacted well to stab his shot past Hassan.
Singapore did manage to pull one back two minutes from time when Fazrul scored from a yard out, after Christopher van Huizen's corner had been nodded into the six-yard box by Safuwan Baharudin.
Still, it was too little too late for Stange's charges as Afghanistan held on for a deserving victory to keep alive their Asian Cup hopes.
Afghanistan: Ovays Azizi, Modijeb Jamali, Mohammed Hashemi, Masih Saighani, Hassan Amin, Kanischka Taher (Ahmad Hatifi 90'), Abassin Alikhil, Faysal Shayesteh (Josef Shirdel 77'), Zubayr Amiri, Norollah Amiri, Khaibar Amani (Omid Popalzay 60')
Singapore: Hassan Sunny, Juma'at Jantan (Al-Qaasimy Rahman 76'), Zulfahmi Arifin (Khairul Nizam 73'), Afiq Yunos, Shakir Hamzah, Safuwan Baharudin, Hariss Harun, Yasir Hanapi, Shahril Ishak (Christopher van Huizen 62'), Hafiz Abu Sujad, Fazrul Nawaz
