Welsh hopes of qualifying automatically for Euro 2024 were dented by a 1-1 draw in Armenia.
Lucas Zelarayan came back to haunt Wales again with a fifth-minute opener before a Nair Tiknizyan own goal in first-half stoppage time restored parity.
The draw helps neither side as far as joining already-qualified Turkey in the top two is concerned.
Even beating Turkey in Cardiff on Tuesday would not be enough for Wales should Croatia win their final two fixtures.
If Croatia win those games, then Wales will be involved in the March play-offs.
Armenia’s chances of a top-two place are almost certainly over, barring a Croatia collapse.
Wales had a score to settle with Armenia after their humiliating 4-2 defeat in Cardiff five months ago, a result which left them playing catch-up in the race for next summer’s tournament in Germany.
Rob Page’s side also had to turn the tide of history as Wales had never beaten Armenia in three previous meetings.
Wales were unchanged from the side that produced last month’s stunning 2-1 win over World Cup semi-finalists Croatia.
Brennan Johnson missed that game through injury and the Tottenham forward, fresh from his first Spurs goal, had to make do with a place on the bench.
Armenia – ranked 95 in the world and 67 places below Wales – showed nine survivors from the team who had won in Cardiff in June, including Grant-Leon Ranos and Zelarayan who both scored twice then.
Wales were behind inside five minutes after failing to deal with a corner.
Danny Ward hesitated before Joe Rodon’s poor header looped towards Zelarayan, who shifted the ball onto his right foot and found the bottom corner with unerring accuracy.
David Brooks fired over in reply and Neco Williams saw his effort deflected wide after Kieffer Moore had pounced on a home mistake.
Moore headed wide but Wales were generally unable to sustain attacks, with Armenia dangerous on the counter.
Vahan Bichakhchyan drove inches wide from one such raid, and Wales suffered another blow as Chris Mepham’s challenge on Zelarayan earned him a yellow card to rule him out of the Turkey game.
Wales went close after 37 minutes when Williams pulled the ball back into Harry Wilson’s path and goalkeeper Ognjen Cancarevic was at full stretch to save.
Then, just seconds from the interval, Connor Roberts sent over a long throw and Tiknizyan, under pressure from Rodon, headed into his own net.
Johnson replaced Brooks within three minutes of the restart and the contest was developing a spicy edge, with Varazdat Haroyan cautioned for chopping down Wilson and Ethan Ampadu similarly punished for his reaction to the challenge.
Armenia went mightily close as Bichakhchyan’s chip drifted over the head of Ward and onto the crossbar.
The crowd held its breath as Zelarayan seemed certain to bury the rebound but instead, the game’s best player sliced it over.
Armenia were slowly turning the screw, though Cancarevic was tested from outside the box by Jordan James and needed a second attempt to gather.
Eduard Spertsyan had a clear sight of goal before being denied by one of an increasing number of last-gasp Welsh blocks.
Moore’s header was held by Cancarevic and in a frantic finale, Ward produced a flying stop to deny substitute Edgar Sevikyan, who later shot wide with the goal at his mercy.
