Wales suffered a penalty shoot-out defeat to Bosnia and Herzegovina in Cardiff to end their 2026 World Cup dreams.
Brennan Johnson and Neco Williams both missed in the shootout as Kerim Alajbegovic's winning spot-kick saw Bosnia set up a home World Cup play-off final against Italy on Tuesday.
Wales' play-off semi-final heartbreak means they miss out on qualifying for back-to-back World Cups.
Edin Dzeko's late header forced extra time after Dan James had stunningly volleyed Wales ahead early in the second half.
Craig Bellamy's side will return to Cardiff on Tuesday to face Northern Ireland, who were defeated by Italy in their play-off semi-final, in a friendly.
Wales will feel they should be hosting Italy on Tuesday for a spot at the World Cup, having been four minutes from booking a play-off final against the four-time winners.
Harry Wilson looked like breaking the deadlock at the Cardiff City Stadium as he struck the post and forced a save from a free-kick with Wales' only shot on target of the first half against a physical Bosnia side.
But it was James who delivered the breakthrough six minutes into the second half with a superb volleyed strike from around 25 yards.
The Leeds winger latched onto a loose ball and caught Bosnia goalkeeper Nikola Vasilj out with a powerful shot to give Wales the lead.
An end-to-end encounter then ensued as James hit the bar with a deflected shot, before Wales goalkeeper Karl Darlow made a fabulous stop to somehow claw out Ermedin Demirovic's header at his near post.
But Darlow could not keep out Dzeko's header as the 40-year-old Bosnia captain rose highest at a corner to equalise in the 86th minute for his 73rd national team goal.
The ex-Manchester City striker was then involved in a touchline clash with Bellamy in extra time, which saw Dzeko booked.
Neither side could find a winner in extra time, with Wilson missing the best chance, taking the tie to penalties, where Bosnia prevailed in a cruel repeat of Wales' Euro 2024 play-off exit.
Wales' Dan James:
"Really tough to take. I think we played incredibly tonight. It was unfortunate for them to score late, and then I thought after extra time that we were the only team that was going to go on to win it.
"It was a credit to ourselves, we've come so far, and it just wasn't meant to be tonight.
"I think we were unfortunate not to get a second. We had chances, I hit the bar, and it just didn't go in, giving them that little bit of chance and confidence to try and get a goal and equalise, and that's what they did.
"Credit to us for going to extra time and dominating the game, we created lots of chances, but it goes to penalties, and that's how it is."
Your Site News' Geraint Hughes at the Cardiff City Stadium:
"Oh my word, it's happened again to Wales.
"Exactly two years ago to the very day, they lost a shootout against Poland to miss out on qualifying for Euro 2024. The penalty curse has struck twice.
"What a contrast at full-time, with the Bosnian players in one corner of the stadium celebrating widely while every Wales player and member of the backroom staff are in a huddle with Craig Bellamy in the middle of it. He's pacing around and talking to them, clearly with passion.
"This will hurt."
Wales boss Craig Bellamy:
"We're going to hurt. I haven't really felt this towards a group of players, because I've probably never had a group of players for myself as a coach.
"Getting to back-to-back World Cups was really our target. To know you've not got there, and when you see players really disappointed, it hurts you more.
"I hurt tonight as it sinks in now. It will be a sleepless night, difficult to sleep off the back of this one. But it makes me even more determined tomorrow.
"The sun will rise, and I'm going to watch that sun rise. Then straight away, how do I go again? How do I improve? How does this team get better?
"Let's get over tonight, but there's a bright future. If I was playing, imagine looking forward to what's coming up.
"As a group of players, you have the Nations League coming up. Group A.
"You have a home nation Euros coming. It's not a bad time to be a Welsh footballer."
On missed penalties:
"It's a hard one and we practise pens. We've done all our research on it, we spent all week doing it. So we couldn't have done any more on penalties. Honestly, I don't believe in luck on pens.
"You've got to be prepared and rehearse them every day in training. The analysis on penalties, we went really through it. That leaves me more bewildered when they missed the first one. I thought, 'yeah, this is exactly what we practise for', but it wasn't the case."
