Italy failed to qualify for a third consecutive edition of the World Cup as they lost 4-1 in a penalty shoot-out to Bosnia-Herzegovina, having had Alessandro Bastoni sent off in a tense 1-1 draw in Zenica.

Moise Kean punished an early mistake from Nikola Vasilj to put Italy ahead, but the Azzurri spent long periods penned back in their own half after Bastoni was sent off for a last-man foul late in the first half.

Haris Tabakovic finally broke their resistance in the 79th minute, and though the hosts could not find a winner in extra time, they took four perfect penalties in the shoot-out.

Italy, by contrast, saw substitutes Francesco Pio Esposito and Bryan Cristante fluff their lines – the former firing over and the latter rattling the crossbar – to ensure their wait for a World Cup appearance will continue for at least four more years.

Italy were gifted the lead against the run of play after 15 minutes, as Vasilj played a dire pass straight to Nicolo Barella, who offloaded to Kean on his left. The Fiorentina striker then opened up his body and curled a tremendous finish into the top-right corner. 

But the hosts were given a major boost in the 41st minute as Memic attempted to dart in behind and Bastoni scythed him down after being caught on his heels as the last man. Clement Turpin immediately brandished a red card, and there would be no VAR reprieve.

The pattern of Bosnia-Herzegovina dominance continued after the interval, with Ermedin Demirovic just failing to meet Amar Memic's cross and substitute Kerim Alajbegovic testing Gianluigi Donnarumma, though Kean wasted a fine chance to make it 2-0 on the break.

With the hosts growing desperate, Donnarumma palmed Benjamin Tahirovic's drive around the post, but when he made another spectacular save to block Edin Dzeko's header, substitute Tabakovic reacted quickest to apply a poacher's finish from a yard out.

Italy were clinging on in the closing stages of regulation time, but they arguably had the best chance in extra time as Vasilj smothered a goalbound header from Esposito.

And Esposito was the first man to blink in the shoot-out as he lashed high over Vasilj's goal. After Cristante joined him in missing the target from Italy's third kick, Esmir Bajraktarevic held his nerve to book Bosnia-Herzegovina's ticket to North America.

Data Debrief: Unwanted history for Italy

Italy are the first former winners of the World Cup to fail to qualify for three consecutive editions of FIFA's flagship tournament. 

By the time they next have a chance to appear at a World Cup, it will have been 16 years since they last did so, and 24 years since they last played a knockout match, having beaten France in the 2006 final.

Italy had something to defend when Kean scored for the sixth successive game for his country, becoming just the fourth Azzurri player to do so after Adolfo Baloncieri in 1928, Luigi Riva in 1969 and Roberto Bettega in 1977. 

But their position unravelled after Bastoni's red card, which made him the first Italy player to be sent off in a World Cup qualifier since Giorgio Chiellini versus Israel in September 2016.

Bosnia-Herzegovina set up camp on the edge of Italy's area from that moment on, and by the end of extra time, they had attempted 30 shots (11 on target) to the visitors' nine (three on target), while they also won the expected goals (xG) battle by 1.73 to 0.86.

Sergej Barbarez's team will now be the opening opponents for World Cup co-hosts Canada on June 11, with Qatar and Switzerland their other opponents in Group B, while Italy will watch from home once again.