Wales' hopes of qualifying automatically for Euro 2024 suffered a potentially devastating blow with a lacklustre draw with Armenia in Yerevan.
Armenia, who inflicted a humiliating defeat on Wales in Cardiff in June, took the lead after just five minutes when Lucas Zelarayan - who scored twice in that 4-2 summer triumph - seized on slack defending to strike powerfully from the edge of the penalty area.
Wales were panicked and frantic but still created chances and equalised shortly before half-time as Armenia's Nair Tiknizyan headed into his own net from a Connor Roberts throw-in.
With both sides needing a win to maintain any realistic chance of automatic qualification, they each attacked desperately after the break, with Armenia's Vahan Bichakchyan hitting the crossbar and Jordan James having a shot saved for Wales.
In truth, the visitors did not deserve to win and, as a result, they are no longer in control of their fate.
Wales must now beat Group D leaders Turkey in Cardiff on Tuesday and hope that Croatia drop points against either bottom side Latvia later on Saturday or against Armenia on Tuesday.
If Wales fail to finish among the group's top two, they will almost certainly have the back-up option of the play-offs in March thanks to the Uefa Nations League.
There is no doubt, though, that this result is damaging for Robert Page and his players, who had their destiny in their own hands before this visit to Yerevan.
But they threw away the opportunity with a wretched performance.
Wales' chances of qualifying appeared in tatters previously during this campaign when they suffered back-to-back defeats against Armenia and Turkey in June.
Losing 4-2 at home to Armenia was particularly damaging, with Page later saying he was "haunted" by his side's capitulation against a team then ranked 71 places below them in the world standings.
If that was the nadir of Page's tenure, the manager rated last month's momentous win over Croatia as the best performance of his time in charge.
Coupled with victory in Latvia in September, the victory against the Croatians had reignited Wales' qualifying hopes and put them in a position where victories against Armenia and Turkey would have guaranteed their place in Germany next summer.
Such was the chastening nature of that previous defeat against Armenia, however, there was still some residual wariness for Wales coming into this game.
Armenia's line-up in Yerevan featured nine of the players who started in Cardiff and Zelarayan, whose majestic volley had lit the fuse for that memorable victory, proved to be a thorn in Wales' side once more.
The home side started positively and, after Wales failed to deal with a corner in the fifth minute, Zelarayan controlled the ball on the edge of the area, evaded two defenders and fired a low shot in off the post.
That goal was fuel to the fire of the atmosphere in Yerevan, with flares lit in the stands and the home crowd fervently getting behind their team, who also still had a chance of qualifying for Euro 2024.
The action on the pitch was every bit as frenetic as Wales sought a swift reply, with David Brooks shooting narrowly over before Neco Williams had a shot deflected wide.
'Lack of poise'
Wales were creating chances but playing with none of the poise or control they had demonstrated against Croatia.
Matters worsened when Chris Mepham received a first-half yellow card which means he will be suspended for Tuesday's game against Turkey, and there was another fright when Kieffer Moore went down clutching his ankle before getting back to his feet to continue.
Despite their mounting problems, Wales equalised just before the half-time whistle. It was unclear at first who had scored as Joe Rodon appeared to have connected with Robert's throw, but replays showed the Wales centre-back's flick-on had hit Tiknizyan, who headed into his own net.
With both sides needing to win to have a realistic chance of qualifying automatically for Euro 2024, there was a desperation to their play in the second half.
Tempers flared with yellow cards shown to players on both teams and, just as Wales seemed to be settling and quietening the crowd a little, Bichakchyan rattled the crossbar to swing the momentum back in Armenia's direction.
Wales brought on Brennan Johnson and Daniel James in the hope that their pace and direct running could help conjure the winning goal, but they were still lacking in the final third.
But they could not find a way through. Instead, it was Armenia who came closest to a winner as substitute Edgar Sevikyan forced Danny Ward into a stoppage-time save.
As the draw also did nothing to help Armenia's bid to qualify for Euro 2024, an underwhelming silence momentarily befell the Vazgen Sargsyan Republican Stadium at the final whistle.
There was frustration among the home crowd, but nothing quite like the despair felt by Wales, who will likely need to take the long road if they are to make it to a fourth major tournament in eight years.