South Korea slipped to a 3-2 defeat against Qatar in Doha on Tuesday, with their World Cup qualifying fate still far from certain with two Group A games to go.
Uli Stielike's men are second in the group - in a qualifying berth - but they remain just a point clear of third-placed Uzbekistan after Qatar held off a second-half fightback with Hasan Al Haydos' brace and a goal from Akram Afif.
South Korea last failed to qualify for a World Cup in 1982, but they have not won away from home in over a year and struggled in the opening hour against their bottom-of-the-table hosts.
Al Haydos' 25th-minute free-kick opened the scoring and Afif doubled Qatar's lead after 51 minutes, before Ki Sung-yueng's goal prompted a strong response.
Hwang Hee-chan restored parity and appeared to set the Koreans up for a dramatic win, until Al Haydos struck again to clinch the points.
Having drawn a blank on trips to Iran, Malaysia - to play Syria - and China, Stielike was visibly irked by the visitors' laboured early attempts to test Saad Al Sheeb, Lee Jae-sung's curler finally drawing a first notable save after 21 minutes.
And the breakthrough then came at the other end, from a 20-yard free-kick controversially given against Choi Chul-soon, as Al Haydos fired a fine strike inside the right-hand post.
Hwang Hee-chan dragged wide as South Korea sought a swift response, but an injury to star man Son Heung-min dealt a further blow, before Al Sheeb brilliantly denied substitute Lee Keun-ho.
Qatar threatened again at the start of the second half and, after shooting wide from close range, Al Haydos turned provider for a second goal, Afif driving high past Kwoun Sun-tae.
Back came South Korea and Al Sheeb blocked Hwang Il-su's strike, but could not prevent Ki's side-footed effort from finding the bottom-right corner.
And, with that goal, the visitors finally built momentum, the equaliser arriving as Hwang Hee-chan met Hwang Il-su's knockdown with a thumping volley.
But, as South Korea went chasing a winner, they were caught out at the back once more and Al Haydos slotted into the bottom-right corner, sealing victory with 16 minutes remaining.