Italy, four-time champions, will once again miss the FIFA World Cup for the third straight time after a nervy defeat to Bosnia and Herzegovina in the qualification play-off final.
Italy started strongly and took the lead through Moise Kean in the 15th minute, but crumbled under pressure, with Alessandro Bastoni being sent off for chopping down Amar Memic four minutes before half-time.
Haris Tabakovic pulled Bosnia back in the game with an equaliser in the 79th minute, and Italy's misery deepened in the shoot-out as Francesco Pio Esposito blazed their opening penalty over.
Bryan Cristante then struck the bar, and when Esmir Bajraktarevic squeezed his effort under Gianluigi Donnarumma, the contest had effectively slipped away.
Italy coach Gennaro Gattuso said he was proud of the boys, but the defeat will raise questions about his status, and there will be reflection from the football federation.
