Wales have failed to qualify for Euro 2024 after losing to Poland in a penalty-shootout in Cardiff.
The game went to penalties after it remained 0-0 after 90 minutes and extra-time at the Cardiff City Stadium.
Poland won the penalty shoot-out 5-4, goalkeeper Wojciech Szczesny – a former Arsenal player – saving the crucial spot-kick from Leeds winger Daniel James.
Poland converted five perfect penalties with Robert Lewandowski, Sebastian Szymanski, Przemyslaw Frankowski, Nicola Zalewski and Krzysztof Piatek all successful against Danny Ward.
It means Poland are through to their fifth successive European tournament.
They will be in Group D with France, the Netherlands and Austria at the tournament in Germany, which begins in June.
Wales have qualified for the last two UEFA European Football Championships, reaching the semi-finals in 2016 and the round of 16 in the delayed 2021 tournament.
Defeat to Poland “hurts”, manager Rob Page told S4C.
“It’s a cruel game, that’s what I’ve said to the players – one kick away from qualifying,” he added.
“I thought we were the better team – my message to the players at half-time was we are the better team, we will win this game.
“It’s so disappointing but look how far we’ve come – there’s something good happening with this group.
“We rallied around Daniel James – he had the bravery to take that penalty. I am so proud of that group.”
The defeat comes after Wales secured a 4-1 victory over Finland in the play-off semi-final last Thursday.
They needed to secure a win in both play-off matches in order to qualify for the tournament in Germany later this year.
Rob Page’s side have lost several experienced players since the World Cup in 2022, including midfielder Joe Allen and former captain Gareth Bale.
England have already reached Euro 2024 as the winners of qualifying Group C and Scotland as the runners-up in qualifying Group A.