Bangladesh's hopes of reaching the AFC U-20 Asian Cup finals suffered another major blow as Gerard Jones's side slumped to a 3-0 defeat against Syria in their second Group B qualifier in Tashkent on Thursday.
The result leaves Bangladesh without a point from two matches, following Monday's 2-0 defeat to hosts Uzbekistan. The eight group winners and seven best runners-up will qualify for next year's finals in China.
Syria dominated the opening exchanges at the Do'stlik Stadium and eventually broke the deadlock in the 44th minute when Alan Mamo struck a low effort from outside the box. Mario Stelios Al-Herak doubled Syria's advantage in first-half stoppage time after capitalising on a misplaced Bangladesh pass.
Bangladesh showed greater urgency after the interval, but Syria remained dangerous. Goalkeeper Raj Chowdhury made several important saves to keep his side within touching distance.
The decisive third goal arrived late, however, when Alnazar's seemingly innocuous low free-kick rolled through the Bangladesh defence and into the net.
Bangladesh will now face India in their final Group B match on 6 September, needing a remarkable turnaround to keep their qualification hopes alive.