Italy lost on penalties to Bosnia meaning they missed out on a third successive World Cup, as qualification for the tournament finished on Tuesday.
The four-time world champions had taken an early lead but the match swung on a first-half sending off, allowing Bosnia a route back into the game, with the game ending 1-1 after extra time.
The home side then won the shootout, meaning their 40-year-old captain Edin Dzeko is now set to become one of the oldest players in World Cup history.
Elswhere Viktor Gyokeres was the hero for Sweden as his 88th-minute goal secured a 3-2 win over Poland, but there was heartbreak for Scandinavian neighbours Denmark as they lost a shootout away to the Czech Republic after a 2-2 draw.
Turkey complete the UEFA line-up as they edged past Kosovo 1-0.
DR Congo and Iraq will also head to Canada, Mexico and the USA after securing respective wins over Jamaica and Bolivia.
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