Cardiff, United Kingdom: Wales boss Rob Page said missing out on Euro 2024 was "cruel" on his players after Poland edged a penalty shootout 5-4 to qualify in Cardiff on Tuesday.
After the sides could not be separated in a tense 0-0 draw, Leeds winger Dan James was the only player to fail to score in the shootout.
Poland's five perfect spot-kicks earned them a place alongside France, the Netherlands and Austria in a tough Group D at Euro 2024 in Germany this summer.
"We created a good, emotional game. This is a very important day for us," said Poland coach Michal Probierz.
Wales' new generation, shorn of the talismanic presence of the retired Gareth Bale, came up short by the finest of margins in heartbreaking fashion for the home fans and their manager at the Cardiff City Stadium.
"It's a cruel game, that's what I've said to the players, one kick away from qualifying. It hurts," said Page.
"We'll be bigger and stronger for having gone through this horrible experience. This group is going somewhere. There is a lot more to come, there are good times ahead."
Despite possessing the threat of Barcelona star Robert Lewandowski up front, Poland failed to register a single shot on target in the 120 minutes.
However, the visitors found their range from the spot as Lewandowski, Sebastian Szymanski, Przemyslaw Frankowski, Nicola Zalewski and Krzysztof Piatek confidently fired home.
James had to score to keep his country in it, but Wojciech Szczesny dived low to his right to send Poland to a fifth consecutive Euros.
Only once before have they managed to get out of the group stages of the European Championship, reaching the quarter-finals in 2016.
Both sides were in free-scoring form in the playoff semi-finals on Thursday as Wales brushed aside Finland 4-1, while Poland trashed Estonia 5-1.
However, it was a far tighter and more tense affair with qualification on the line.
Page shuffled his forward options as despite scoring against the Finns, David Brooks dropped to the bench to make way for Kieffer Moore.
Moore's physical presence has been a vital weapon in Wales' arsenal since Page took charge four years ago and provided a bigger threat than Lewandowski at the other end.
At the end of a first half short on goalmouth action, the hosts thought they had taken the lead in stoppage time.
Ben Davies headed in from Moore's knockdown but the Tottenham defender had strayed centimetres offside.
Szczesny denied Moore the opener just two minutes into the second period with a spectacular save to prevent the on-loan Ipswich striker's header looping into the top corner.
Poland's away form had already cost them automatic qualification after defeats on the road to Albania, the Czech Republic and Moldova.
Wales goalkeeper Danny Ward has not played a minute of club football for Leicester this season, yet he was not tested before the shootout.
The home side finished the 90 minutes in the ascendency but lacked the creative spark to make the breakthrough that was so often provided over the past decade by Bale or the injury-plagued Aaron Ramsey, who was an unused substitute.
The tables were turned in Wales' first ever period of extra-time in international football as Page's exhausted men clung on for penalties.
Jakub Piotrowski came closest to winning the game for the Poles as his effort from the edge of the box flew inches past the far post.
Wales saw out the final few seconds with 10 men as Chris Mepham was shown a second yellow card.
But their first experience of penalties was a sour one despite Davies, Moore, Harry Wilson and Neco Williams scoring their first four efforts.