Having remained silent in their first World Cup game against England Iran players have sung the national anthem ahead of their clash against Wales on Friday night, as some fans were pictured in tears and others jeered and whistled in the stands.

Some Iran fans confiscated Persian pre-revolutionary Iranian flags from others and shouted insults at those wearing shirts with the slogan of the country’s protest movement, “Woman, Life, Freedom”.

In the match itself, Rouzbeh Cheshmi scored in the eighth minute of stoppage time to end a tense stalemate  and put Iran on course for a 2-0 victory in Group B.

Cheshmi’s strike from outside the box was just beyond the diving reach of Wales back-up goalkeeper Danny Ward, who was pressed into duty when custodian Wayne Hennessey was sent off in the 86th minute.

Roozbeh Cheshmi is mobbed by teammates after scoring Iran’s opening goal against Wales. Photo: Getty

Hennessy became the first player to be sent off at Qatar 2022, and only the third goalkeeper in the history of World Cup final tournaments, following his crude challenge on Mehdi Taremi well outside the penalty area.

Ramin Rezaeian added a second goal in the dying seconds and Iran celebrated wildly while some of the Welsh players dropped in disbelief to the field.

The game was still in the balance when Hennessy was shown a red card, after a VAR check, in the 86th minute for a high challenge on Mehdi Taremi well outside his penalty area.

Gareth Bale, who was making a record 110th appearance for Wales, applauds supporters after the defeat. Photo Getty

Gareth Bale made a record 110th appearance for Wales, but the Welsh appeared sluggish.

Wales was making its first appearance at a World Cup since 1958 and Bale admitted he was “gutted” by the defeat.

“It’s gutting, we’re gutted, there’s no other way to say it,” Bale said.

“We fought to the last seconds but it’s difficult to take. But we have to pick ourselves up straight away, it’s going to be difficult but we have one game left.”

Wales manager Rob Page said: “Our performance before the red card was not acceptable.

“We hoped it would all come together today, but we were nowhere near the levels we’ve set and the standards we’ve set in recent games.

“One or two you can carry, but when there are so many off days there is only one outcome.

“I always take responsibility, that’s my team. The sending off didn’t help of course but at that point we had five forwards on the pitch so couldn’t get a defensive shape.”

They might have fallen behind earlier when Iran hit both posts in the space of a few seconds.

First Sardar Azmoun raced clear, only to shoot against the right-hand post, then Ali Gholizadeh curled the follow-up against the other post.

Finally, Azmoun headed that rebound straight at Hennessey.

Wales’ best effort was a rising shot from defender Ben Davies, which was tipped over by the goalkeeper.

The result was some redemption for the Iranians who were humilated 6-2 in their opening game against England.

The win moves Iran to three points in Group B, two more than Wales, which was held to a 1-1 draw by the United States in its opener.

Wales next faces a must-win showdown against England, but not even victory will guarantee its progress through to the knockout rounds.

-AP with the ABC