Syria’s unlikely 2018 World Cup dream is over after Tim Cahill’s extra-time header saw Australia progress 3-2 on aggregate to the final qualifying tie.
Omar Al Somah gave the civil war-torn nation hope of reaching Russia when he gave them an early lead in Sydney.
But Cahill, 37, quickly equalised with the first of his two headed goals.
Syria, who drew 1-1 in the first leg, were reduced to 10 men when Mahmoud Al Mawas was sent off before Cahill nodded in Robbie Kruse’s cross for the winner.
Australia will now play either Panama, Honduras or the US from the CONCACAF section for a place in the finals.
Syria was given real hope of reaching its first World Cup finals when a loose Mark Milligan pass let Al Somah charge through to score a sixth-minute opener with a low left-footed shot.
But Hertha Berlin winger Mathew Leckie engineered parity for the hosts when he provided the perfect cross for former Everton midfielder Cahill’s first on 13 minutes.
The introduction of Huddersfield Town midfielder Aaron Mooy from the bench was then pivotal.
Australia manager Ange Postecoglou surprisingly left the 27-year-old out of his starting line-up, but the home side were instantly improved by his presence.
Indeed it was only Syria goalkeeper Ibrahim Almeh’s heroics that denied Celtic’s Tom Rogic and Leckie from sealing Australia’s progress in the second half.
Syria defended resolutely and admirably got to extra time, but their task became harder when Al Mawas saw red for a second booking for bringing down Kruse.
With penalties looming, Cahill produced a trademark last-gasp header to score his 50th goal for Australia – more than any other player for the country.
Yet despite being a man down, the visitors almost snatched an equaliser to take the tie to penalties when Al Somah’s free-kick hit the post in the 121st minute.
