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India's wait for a maiden knockout round berth in the Asian Cup continued as they crashed out of the continental football showpiece after suffering a 0-1 defeat to Syria in their last group match in Al Khor, Qatar, on Tuesday.
Substitute Omar Khribin scored the all-important goal in the 76th minute to keep Syria in contention for a round of 16 berth.
India finished at the bottom of the four-team Group B after losing all their three matches and without scoring any goal.
Tuesday's match will certainly be the swansong Asian Cup game for talisman Sunil Chhetri, who had appeared in the two earlier editions also -- in 2011 and 2019.
The 39-year-old Chhetri, who is in the twilight of his illustrious career, has scored four goals -- two each in 2011 and 2019 -- in nine appearances to be the highest scorer from India in the continental showpiece.
India had also failed to make it to the knockout round in 1984, 2011 and 2019 editions of the tournament. They had finished runner-up in 1964 when the winner was decided after a round-robin league among four participating teams.
India, under Igor Stimac, will return home after yet another disappointing show in the continental showpiece. The Indians had won one match -- against Thailand (4-1) -- in the 2019 edition, but this time, they fired a blank, returning home without any point.
The Indians had lost to Australia (0-2) and Uzbekistan (0-3) in their earlier two group matches.
The initial minutes of the match saw India going on the offensive and there were some threatening runs from Mahesh Naorem and Lallianzuala Chhangte but they did not lead to a clear chance.
But as the match wore on, the Syrians began stamping their authority and went on a rampage towards the end of the first half.
In the seventh minute, Pablo Sabbag's header off a corner kick was saved on the goal-line by goalkeeper Gurpreet Singh Sandhu.
Soon, Sandhu was called into action as he blocked a shot from Ibrahim Hesar but the rebound fell on another Syrian player Ezequiel Ham whose effort was brilliantly thwarted by Subhasish Bose.
The Indian citadel was under siege for long periods of time and the Syrians appealed for a Video Referee Assistant decision after one of their players was denied a shot inside the box.
In the added time of the first half, captain Sunil Chhetri, who had an ordinary outing in this tournament by his standards, made a long range effort but was off the target.
India got three shots in the first half as against around a dozen for the Syrians.
India suffered a jolt in the first minute of the second half with defensive mainstay Sandesh Jhingan suffering an injury and being substituted by Nikhil Poojary. Mahesh Naorem was also replaced by Udanta Singh at the beginning of second half.
The stalemate continued even as Igor Stimac introduced Sahal Abdul Samad in the 65th minute for his first match of the tournament as he recovered from an injury.
Just before that, Syria had a chance to take the lead but Omar Khribin's free header sailed over the bar.
With the match entering the last 20 minutes, the Syrians pressed for goal as they needed a win to be in contention for a knockout berth. The Indians defended desperately with almost all of them in their own half.
The Syrians were not to be denied a goal to the disappointment of the large number of Indian supporters who filled the stadium.
Ibrahim Hesar was able to work through to the left edge of the box and his pass found Khribin who outwitted Rahul Bheke before drilling a low shot past Gurpreet.
The Indians made a last-ditch effort to find an equaliser towards the end of the match with more men upfront, but a goal eluded them.