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India threw away a first-half lead and went down 1-2 to Syria in their opening Group C match in the AFC Youth Football Championship in Kuala Lumpur, Malaysia.
The Indian under-19 footballers, included in the tournament following the late withdrawal of Turkmenistan, took the lead at the half hour mark through striker Vimal Pariyar.
But the Indians failed to make good of the advantage, as defender Safir Al Atasi equalised for Syria ten minutes into the second half before Abdul Al Razak Al Housain scored the winner for the 1994 champions in the 77th minute.
India's best performance in the AFC Youth Championship came three decades ago, when they shared the title with Iran in Thailand in 1974.
Meanwhile, Uzbekistan hammered lowly-rated Laos 5-2 in another match in the same group.
The top two teams from each of the four groups advance to knock-out stage, which will commence with the quarter-finals.
The top four teams in the competition will qualify for the FIFA World Youth Championship, to be held in the Netherlands next year.
Korea are the defending champions. They beat Japan in the 2002 final in Qatar.