In what was a first shootout for Wales’ men in a competitive match, Daniel James missed the only spot-kick – saved by Wojciech Szczesny – while Poland converted all five.
It was a desperately painful way for Robert Page and his players to lose, beaten by a Poland side who failed to register a single shot on target during the entire 120 minutes before the shootout.
Robert Lewandowski’s side can now look forward to joining France, Netherlands and Austria in Group D at this summer’s Euros in Germany.
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Crestfallen Wales must watch from afar having failed to qualify for a European Championship for the first time since 2012.
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The stunned expressions on the players’ faces and the momentary silence which befell the home crowd spoke volumes.
It will take time to digest the gut-wrenching nature of this defeat, longer before Page, his players and Football Association of Wales bosses can decide what it means for the team’s long-term future.
For now, they must endure this pain.
Having become used to qualifying for major tournaments, this was a moment of heartbreak to rank alongside the most devastating near misses which had come to define Welsh football in bygone eras.
This will hurt for some time.
Anxious intensity
In a tentative first half gripped by nerves, Wales captain Ben Davies had a goal disallowed as he headed in from an offside position.
Chances were still a precious commodity after the break, with Kieffer Moore’s header forcing Szczesny into a fine save while Poland’s fearsome striker Lewandowski was limited to a diving header which he sent over the crossbar.
The tension only increased in extra time as Jakub Piotrowski came within inches of an opener with a fabulous curling long-range shot.
Exhausted in the second half of extra time, Wales had to defend resolutely in the face of heavy Polish pressure.
Wales centre-back Chris Mepham was sent off after receiving a second yellow card in the final minute of extra time, but Page’s side held on for penalties.
However, Poland converted all five of their spot-kicks before Leeds United winger James saw his saved by Juventus keeper Szczesny to break Welsh hearts.
Poland goalkeeper watches ball go into net
Ben Davies saw his effort before half-time ruled out for offside
Cardiff City Stadium has become famous for its atmosphere on nights like these for Wales, but rarely has the ground fizzed with such intensity.
Both teams seemed anxious during a tense opening as they tried to gain an early foothold in the game, neither passing with much fluency or able to build coherent attacks.
It was telling that Wales’ first chance came from a set-piece – Davies heading over from a Harry Wilson corner – while a Connor Roberts long throw also raised alarm in the Polish penalty area.
This was a typical high-stakes knockout match – all probing and jabbing, little in the way of decisive blows.
Just for a moment, Wales thought they might have found one, again from a set-piece.
Davies nodded in from Moore’s header back across goal – but the fact Wales’ players all looked to the linesman even before he raised his flag suggested they knew the goal would be disallowed for offside.
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Moore offered another reminder of his aerial threat early in the second half when his looping header was superbly clawed away by Szczesny.
Lewandowski, unusually subdued until that point, had his first sight on goal as he headed over from a Piotr Zielinski corner.
The Barcelona striker then fired a low shot wide as the clock ticked towards 90 minutes and the spectre of extra time loomed.
This was the first time Wales’ men had been involved in extra time in a competitive match, and it looked like they would be denied a first penalty shootout when Piotrowski’s 25-yard effort curled narrowly wide.
In the second half of extra time, Wales retreated deep into their own half and invited constant Polish pressure, but the visitors still struggled to create genuine scoring opportunities.
It did not matter as Poland were faultless in the shootout, before Szczesny made himself the hero by parrying James’ effort wide to spark wild celebrations among the travelling fans.
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