Substitute Roozbeh Cheshmi struck from 20 yards nine minutes into stoppage time, before Ramin Rezaeian finished off a counter-attack to seal victory for a revitalized Iran side, who have renewed hope of reaching the knockout stages for the first time in their history.

Those were decisive blows to Welsh prospects of victory, which had all but vanished when goalkeeper Wayne Hennessey was sent off with four minutes of normal time remaining, following a video assistant referee check, for a reckless challenge on Medhi Taremi.

As they did in their opening draw with the United States, Wales started poorly and had the video assistant referee (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 national anthem this time — having declined 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 defense exposed and the onrushing Hennessey brought down Taremi.

Hennessey was initially shown a yellow card, but it was changed to a red after the referee was advised to check on the pitchside monitor, with the 35-year-old becoming only the third keeper to be sent off at a World Cup.

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 unrecognizable from the team thrashed 6-2 by England in their first match and fully deserved this win.

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.