Italy 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 away to Bosnia.

Azzurri substitutes Pio Esposito and Bryan Cristante missed from 12 yards in Zenica, allowing Esmir Bajraktarevic to convert the hosts' 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 eventually levelled in the 79th minute.

Bosnia, who will play at a second World Cup following their debut in 2014, will be in Group B at this summer's tournament alongside co-hosts Canada, Qatar and Switzerland.