Wales' hopes of automatic qualification for next year's World Cup were dealt a significant blow as Estonia ground out a 0-0 draw at the Cardiff City Stadium.
Sitting seven points off Belgium with two games in hand, Robert Page's team failed to create enough against a side ranked almost 100 places below them and missed out on a desperately needed three points to stay in touch with the group leaders.
Gareth Bale hit the woodwork late in the game on the rebound from his own effort, while Tyler Roberts was denied by Karl Hein when played clean through and Harry Wilson sidefooted wide from a good position in the opening minute.
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Estonia, who had scored first in each of their three previous qualifiers, came close themselves when Mattias Kait struck the bar in the final minutes of the opening half before slowing the match down in its final stages to secure their first point in Group E, and dent Wales' hopes of automatic qualification.
Twenty shots, no goals from toothless Wales
The noise of Land of my Fathers, ringing around the Cardiff City Stadium for the first time in two years, had barely died down by the time Wilson was played through by Chris Gunter's surging run and fired wide of Hein's left-hand post when unmarked from 12 yards.
That looked like setting the tone for Wales' intensity, instead frustration soon grew into the hosts' play and clear-cut chances came at a premium.
There were opportunities, Bale should have found the target with a curling 20-yard effort and Roberts fired wide from a tight angle, but with a moment of individual brilliance, Estonia came closest to finding an opener before the break, with Kait's first-time effort bouncing off the bar and behind when left in acres of space.
The tempo was upped after half-time while a Wales goal still remained elusive, with a Bale bullet header denied by a strong Hein save at his near post.
The 19-year-old Arsenal goalkeeper, playing only his second competitive international game, would prove his side's saviour in the second 45 minutes and raced off his line to deny Roberts when clean through, turning his low effort behind with his legs.
He looked certain to be beaten late on as Wales piled bodies forward with time running out, and it appeared the moment had come when he could only palm Bale's goalbound effort back into his path in the final minutes.
But the Wales skipper summed up his country's night by heading the rebound against the woodwork and away to safety, as their hopes of victory faded - so too, perhaps, that of automatic qualification.
What the manager said...
Wales manager Robert Page tells Sky Sports: "It's pure frustration. We knew what they were going to do, we started the game really brightly. We've got to score a minute in, and if we do it's a different game.
"When you're on top, it's important to score goals. We weren't quite clinical enough. In the past we've won games late on, had the rub of the green and it has dropped for us but today it just did not.
"It feels like a defeat playing against a team bottom of the table. We've got to build on it, be more clinical and get a different result."
Bale: It's not over yet
Wales captain Gareth Bale on Sky Sports:
"I feel like we played well, moved the ball, were a constant threat, it's just one of those nights where we didn't take our chances.
"It's been a while since we had that many, we had a few clear-cut chances, it's disappointing - just frustrating.
"There's a long way to go, a lot of games to go. We can't get too down, take the positives and try to be more ruthless in the next game."
Wales visit Czech Republic in their next World Cup Qualifier on Friday, October 8, live on Sky Sports; kick-off at 7.45pm.