Four-time champions Italy failed to qualify for a third straight World Cup after being beaten in a penalty shootout with 10 men at 66th-ranked Bosnia and Herzegovina in the European playoffs on Tuesday (Wednesday AEDT).
Moise Kean scored early for Italy, but Azzurri centre back Alessandro Bastoni was sent off with a direct red card before the break and Bosnia substitute Haris Tabakovic equalised in the 79th to send the game into extra time.
The defeat added more misery for Italy's once-proud national team after being eliminated by Sweden and North Macedonia, respectively, in the qualifying playoffs for the previous two World Cups.
"It's too easy to say what's working and what's not working," Italy coach Gennaro Gattuso said.
"The fact is that Italy has failed to qualify for three World Cups. We're having a tough time achieving our goals, both with the national team and with our clubs.
"I want to personally apologise since we didn't make it."
Bosnia won the shootout 4-1 and qualified for the first time since 2014, their only previous appearance.
In the shootout, Pio Esposito and Bryan Cristante missed their spot kicks and US-born Esmir Bajraktarevic converted the decisive penalty for Bosnia.
In Tuesday's other European playoff finals, Sweden, Turkey and the Czech Republic each qualified. Sweden edged out Poland 3-2; Turkey beat Kosovo 1-0; and the Czechs won in a shootout.
Victory for Turkey meant they have qualified in Group D along with the Socceroos, the United States and Paraguay.
Italy's latest ouster means that the 1934, 1938, 1982 and 2006 champions will go at least 16 years without even playing a match at soccer's biggest event.
Italy's World Cup struggles go back all the way to 2010 and 2014, having failed to advance from their group on both occasions, although the Azzurri did win the European Championship in 2021.
Italy's last World Cup knockout match was when they won the title in 2006 by beating France in a penalty shootout.
The only other World Cup that Italy did not qualify for was in 1958.
Turkey's 1-0 win in Kosovo meant they have reached soccer's biggest stage for the first time since 2002.
Kosovo had the best chance of an entertaining first half, but Turkey goalkeeper Ugurcan Cakır pulled off a superb one-handed save to push Fisnik Asllani's strike on to the crossbar.
Turkey, ranked 25th in the world, got the breakthrough eight minutes into the second half. Kerem Akturkoglu got the finest of touches to ensure Orkun Kokcu's cross-shot went into the far bottom corner.
"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.
In Guadalajara, Mexico, the Democratic Republic of Congo grabbed their finals berth by beating Jamaica 1-0 in their inter-confederation playoff on Tuesday, Axel Tuanzebe netting an extra-time winner to return them to the finals after a 52-year wait.
The former England under-21 international bundled the ball over the line from a corner in the 100th minute, but had to wait while it was checked for a possible handball before being confirmed as a goal.
It was as much as the Congolese deserved, having dominated proceedings in a fast-flowing match without many clear-cut chances at Estadio Guadalajara, which is one of three Mexican venues for the World Cup.
It is the second time DR Congo have qualified for the finals, more than half a century after their initial appearance in 1974 when the country was known as Zaire.
- with Reuters
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