Italy were at a loss of words as they failed to qualify for a third World Cup in a row after Alessandro Bastoni's first-half red card proved costly in a dramatic 4-1 penalty shoot-out defeat to Bosnia and Herzegovina.
Azzurri substitutes Pio Esposito and Bryan Cristante missed from 12 yards in Zenica, allowing Esmir Bajraktarevic to clinch the winning spot-kick following a 1-1 draw after extra time.
Having failed to reach Russia 2018 and Qatar 2022, four-time champions Italy are the first former winners to miss out on three consecutive World Cups.
Gennaro Gattuso's side were on course to progress when Moise Kean capitalised on an error from Bosnia goalkeeper Nikola Vasilj to claim a 15th-minute opener.
But, following Bastoni's 41st-minute dismissal for a last-man foul on Amar Memic, substitute Haris Tabakovic levelled in the 79th minute.
Bosnia will play at a second World Cup following their debut in 2014.
Coach Gattuso was emotional after the heart-breaking loss. "Today the boys didn't deserve a beating like this," Gattuso told RAI.
"We were left with 10 players, we had three decent chances and they barely troubled us. I'm sorry, this is football and I'm proud of my boys.
"It hurts, because we needed it for us, for all of Italy and for our movement. A blow that's difficult to digest."
Gattuso and Italy were incensed when a foul by Tarik Muharemovic on the edge of the area brought just a yellow card early in extra time, but the manager did not want to talk about refereeing decisions.
"I don't want to talk about anything, but today it's unfair," he said.
"I have been in the world of football for years, sometimes I have rejoiced and today I take a beating. It's hard to digest, they surprised me too for the heart they put into it."
Winger Leonardo Spinazzola bemoaned another World Cup miss.
"Italian children will see another World Cup without Italy," said Spinazzola.
"I still can't believe that we went out like this, after playing with 10 men. With grit, we took it to penalties, we could have scored three or four goals and it's really a great disappointment for everyone."
Bosnia manager Sergej Barbarez lauded his team's character.
"I told the players to go on the pitch and enjoy themselves," Barbarez said.
"I've never entered or finished a game calmer, I saw it in their eyes, I really like them, they're guys with character.
"We have guys we're proud of, we're two years ahead of schedule. Now I've told them that we have to go to a tournament every two years."
Turkey through
Turkey qualified for their first World Cup finals since 2004 following victory in Kosovo.
With Arda Guler of Real Madrid and Inter Milan's Hakan Calhanoglu in their team, Turkey were the favourites in the match.
Turkey broke through in the 53rd minute when Kerem Akturkoglu struck from close range.
Turkey, now ranked 22nd in the world, took the final spot in Group D alongside the United States, Paraguay and Australia.
"Thank God. It has been 24 years. Some of us were not even born the last time we qualified, and some were too young to remember. We always dreamed of moments like this," Akturkoglu told Turkish TV.
"We talked about 2002 and the success there, we always dreamed of it. Most of us don’t even remember 2002. Now we will give the next generation something to dream about at the 2026 World Cup. We want to make our country proud," he added.
Meanwhile, Viktor Gyokeres fired Sweden to the finals with a late winner in a 3-2 win over Poland.
Goals from Nicola Zalewski and Karol Swiderski cancelled out efforts from Anthony Elanga and Gustaf Lagerbielke as Poland twice came from behind in Stockholm.
But Arsenal striker Gyokeres settled the play-off two minutes from time, rifling into the roof of the net after Besfort Zeneli's effort struck the right post.
Elsewhere, the Czech Republic qualified for the World Cup for the first time in 20 years after beating Denmark 3-1 on penalties following a 2-2 draw after extra time.
Rasmus Hojlund, Anders Dreyer and Mathias Jensen missed from the spot for the Danes in Prague.
