Sydney FC were made to pay for wasted opportunities as their resuming AFC Champions League campaign got off to a losing start in Qatar on Thursday night.
A brace from Li Shenglong secured Chinese giants Shanghai SIPG, whose side included Socceroos star Aaron Mooy, a 2-1 win over the Sky Blues.
The loss dropped Sydney to the bottom of Group H, and the A-League champions have plenty of work ahead of them in their remaining three group matches if they are to finish in the top two and progress to the knockout stages.
But it could have a much better night for Sydney, who should have led 3-0 in the opening quarter of an hour.
The Sky Blues started strongly and should have gone ahead after five minutes.
Speedster Trent Buhagiar got behind a dozing Shanghai defence before laying a square ball into the path of teammate Kosta Barbarouses.
But with only goalkeeper Chen Wei to beat, the New Zealand international fluffed his shot and failed to even hit the target.
But roles were reversed with a much happier outcome for the Sky Blues three minutes later.
Barbarouses was this time the provider, with Buhagiar running on to the pass and placing his shot into the top corner of the net to give the Australian side a 1-0 lead.
Sydney continued to attack it was only the woodwork which prevented them doubling their advantage in the 14th minute when a header from defender Ben Warland hit the post.
The rebound fell for Sky Blues midfielder Paulo Retre, who blazed his shot over the crossbar.
Barbarouses missed another chance 10 minutes into the second half.
The host of missed chances came back to haunt Sydney.
Not surprisingly it was Mooy who supplied the ball for Shanghai’s equaliser, with his cross headed home by Li in the 63rd minute.
With Sydney tiring visibly, Li then put Shanghai in the 80th minute with another header.
Sydney’s loss was compounded by the stoppage time send-off of goalkeeper Thomas Heward-Belle, who was deputising for the unavailable Andrew Redmayne.
In a brain snap, Heward-Belle charged out of his penalty area and handled the ball, giving the referee no option but to send him off.