Sydney FC are once again set to miss out on the Asian Champions League knockout stage after a 1-0 loss to Jeonbuk Hyundai effectively ended their hopes of progressing in Qatar
Na Sung-eun handed Jeonbuk the lead in the 44th minute and Sydney were never able to peg back the deficit, with the A-League champions left to regret their wastefulness at Al Wakrah Sports Complex.
Sydney had only progressed past the group stage once in their five previous campaigns - reaching the round of 16 in 2016.
They are winless from four games and anchored to the bottom of group H with one point and a poor goal difference, and have just two matches - against Shanghai SIPG and Yokohama F. Marinos - remaining.
The Sky Blues impressed early and almost scored in the 26th minute when Trent Buhagiar whipped in a tantalising ball but Kosta Barbarouses' scrambled toe-poke was well off-target.
On debut, Sydney goalkeeper Adam Pavlesic had a moment to remember when he bravely blocked Gustavo's close-range effort in the 31st minute.
But Buhagiar spurned arguably Sydney's best chance in the 40th minute.
Rhyan Grant did brilliantly to pick out an unmarked Buhagiar on the penalty spot, but the striker dragged his shot wide.
Four minutes later, Jeonbuk made Sydney pay.
Na Sung-eun received the ball in space and his scorching shot nutmegged Michael Zullo, taking a slight deflection and nestling in the bottom corner.
Sydney's intensity didn't drop and they continued to pepper Jeonbuk's goal after the break.
Milos Ninkovic, who was excellent throughout, had a chance saved in the 61st minute, while Barbarouses clipped the side netting two minutes later.
Sydney skipper Alex Wilkinson came desperately close to a rare goal when his excellent 68th-minute header forced Song Bum-keun into a superb one-handed save
Three minutes later, Buhagiar hit a golden opportunity straight at Song - and from there, Sydney were left to rue what might have been.