Wales' first World Cup for 64 years looks set to end at the first hurdle after they suffered a heartbreaking - but deserved - last-ditch defeat against Iran in Qatar.
Substitute Rouzbeh Cheshmi struck from 20 yards deep into added time, before Ramin Rezaeian finished off a counter-attack to seal victory for a revitalised Iran side who have renewed hope of reaching the knockout stages for the first time in their history.
As they did in their opening draw with the United States, Wales started poorly and had VAR to thank for disallowing a goal from Iran's Ali Gholizadeh for offside.
In one of the most highly-charged atmospheres of this World Cup, Iran's players sang their anthem this time - having refused to do so before their opening loss to England in an apparent show of support for anti-government protests in their country - but their own fans booed the anthem and some could be seen crying in the stands.
Roared on by the fervent and almost entirely Iranian crowd, Carlos Queiroz's side were extremely unlucky not to score early in the second half as Sardar Azmoun and Gholizadeh both struck the post within the space of a few seconds.
Wales were utterly ragged and, as they pushed forward in search of the late winning goal they desperately needed, a long ball over the top left the defence exposed and their onrushing goalkeeper Wayne Hennessey was sent off - after a VAR check - for a reckless challenge on Mehdi Taremi.
That set the seal on Wales' fate for this match and, in all likelihood, their hopes of reaching the second round.
While Robert Page's men were just as disjointed as they were against the USA, Iran were unrecognisable from the team thrashed 6-2 by England in their first match and fully deserved this win which breathes new life into their ambitions of progressing to the last 16.
Wales now face the formidable challenge of needing to win their final group match on Tuesday against England, who take on the United States later on Friday.
It is not impossible but, based on how the Group B teams have fared so far in Qatar, Wales' first World Cup for 64 years looks like it is in serious danger of ending at the earliest stage.