Wales have waited 64 years to feature at a World Cup tournament but they have failed to turn up, with Robert Page's side's hopes of advancing to the knockouts hanging by a thread after defeat by Iran.
A reckless challenge from Wayne Hennessey saw the goalkeeper dismissed late on and Iran duly punished the Forest man, scoring two late goals to leave Wales needing a miracle to escape Group B.
Here, Sportsmail's Kieran Gill rates and slates players from both teams, with Hennessey, Aaron Ramsay and Gareth Bale having games to forget in Qatar.
WALES (3-5-2)
Wayne Hennessey – 4
Two super saves to deny Sardar Azmoun and Saeed Ezatolahi. But dear oh dear, that decision to charge out of his box and bring down Mehdi Taremi was rash, reckless and downright daft. The red card was right, and down to 10 men, Wales crumbled.
Chris Mepham – 6
Will have some bruised toes after Morteza Pouraliganji stood on his foot – one of a few examples of Iran winding up the Wales players. Mepham and his fellow defenders were forever on the back foot as Iran took charge. Disappointed to see his clean sheet slip away after his efforts.
Joe Rodon – 6
Rodon’s battle with Azmoun was enthralling. He did just enough to force the Iran striker off balance when he struck the post. Rodon fought to the very end, forever alert to Iran’s counter-attacks at the Ahmed bin Ali Stadium. But ultimately, it's a deflating defeat.
Ben Davies – 6
Left back playing on the left of the Wales back three, Davies looked to progress the ball forward. His passing was accurate and his long balls were probing, while Hossein Hosseini's finger-tip save denied him what might have been a late winner for Wales.
Connor Roberts – 5
VAR got him out of jail after his careless cross-field pass saw Iran pick up possession and score. Thankfully it was offside. Able to get much further forward than he could against the United States. Tantalising crosses from the right wing for 6ft 5in Moore to meet.
Aaron Ramsey – 3
Unlike the United States draw, Wales dominated possession against Iran. But for someone of Ramsey’s standards, he was way too careless on the ball. Iran were forever ready to break forward whenever he gifted them possession. Not good enough from Ramsey.
Ethan Ampadu – 5
Wales’ deepest midfielder but the back three's protection was lacking. Had to commit the odd tactical foul when Iran were countering. Given he’s often the glue holding the midfield together, it was a big call from Wales’ manager to remove Ampadu rather than Ramsey in the second half.
Harry Wilson – 5
Didn't see a great deal of Wilson, who is handy at set-pieces. Substituted before the hour mark as Iran sensed the win was there for the taking. Unfortunately, Wilson and his Wales colleagues can start packing their bags in anticipation of heading home.
Neco Williams – 5
Largely limited against the United States as he tried to tie down Timothy Weah. Flattened by Ramin Rezaeian here, then bundled over by Ali Gholizadeh. Shook off that roughhousing but was sacrificed for Johnson as Wales looked to stop Iran from taking over this group game.
Gareth Bale – 3
Became Wales’ all-time appearance record holder but won't look back on this anonymous performance with any fondness. Bale loves popping up with a moment of magic and Wales looked to him and Ramsey to do something special. It's a pity that both were passengers.
Kieffer Moore – 5
Preferred over James as Moore gives Wales something different up front. Felt he could and should have scored after 11 minutes when he met Roberts’ cross – and that turned out to be Wales’ best chance – but Hosseini’s save was reactive.
SUBS
Dan James (for Wilson, 58) – 5
Came on for Wilson but couldn’t turn the Iran tide which was forever flowing towards Wales’ goal.
Brennan Johnson (for Roberts, 57) – 5
Sometimes substitutes become heroes but the ball never fell for Johnson to have his big moment.
Joe Allen (for Ampadu, 77) – 3
Gave the ball away immediately before both of Iran’s goals – careless, costly and crushing.
Danny Ward (for Ramsey, 87) – 4
His job was to see out the clean sheet. Instead he conceded twice in stoppage time.
SUBS NOT USED
Chris Gunter, Joe Morrell, Tom Lockyer, Jonny Williams, Mark Harris, Adam Davies, Sorba Thomas, Dylan Levitt, Ben Cubango, Rubin Colwill, Matthew Smith
MANAGER
Rob Page – 4
This was a different prospect to the United States game. This time, Wales had more of the ball than their opponents. But they didn't do anything with it. Where was Bale? Where was Ramsey? Iran looked the likelier to win from start to finish and Wales got what they deserved – nothing.
Iran (4-1-4-1): H Hosseini 7.5; Rezaeian 7.5, M Hosseini 7.5, Pouraliganji 7.5, Mohammadi 7; Ezatolahi 7 (Karimi 83); Gholizadeh 7 (Jahanbakhsh 77), Nourollahi 7 (Cheshmi 78), Hajsafi 7 (Torabi 77), Taremi 8; Azmoun 7.5 (Ansarifard 68, 6)
Subs (not used): Beiranvand, Moharrami, Khalilzadeh, Amiri, Niazmand, Kanaanizadegan, Ghoddos, Abedzadeh, Jalali
Manager: Carlos Queiroz 7.5
REFEREE
Mario Escobar – 6
Guatemalan referee let some gamesmanship go. A few Iran players could and should have been carded for their roughness but Escobar let the physicality go in this game. Should have known it was a red for Hennessey without the need for VAR.