Italy’s World Cup hopes came down to a match against Bosnia and Herzegovina in a FIFA Playoff Qualifier.

Those same hopes came to a crashing halt on the wrong end of a 4-1 penalty shootout.

Bosnia and Herzegovina equalized in the closing stages of regulation, and following extra time, the teams advanced to a penalty shootout with a spot in Group B of this summer’s FIFA World Cup on the line. And in the shootout, Bosnia converted their first three attempts while Italy missed two of theirs, giving the home team a chance to book their spot in the World Cup on the fourth attempt.

It was up to Esmir Bajraktarevic, known as the “Milwaukee Messi.” Born in Appleton, Wisconsin, he stepped up to the spot and put Bosnia and Herzegovina into the World Cup:

The converted penalty touched off a wild celebration at Bilino Polje Stadium, and denied Italy a spot in the World Cup for the third consecutive time.

With the elimination, Italy is officially the highest-ranked team not to qualify for the World Cup. Entering play on Tuesday, Italy was ranked 12th in the world in the latest FIFA rankings.

But they will be watching the World Cup from home along with the rest of us.

Italy opened the scoring in the 15th minute with a goal from Moise Kean, giving the visitors an early 1-0 lead. But a crucial moment just before the first half ended set the stage for the dramatic ending. An awkward challenge from Alessandro Bastoni resulted in a red card, leaving Italy a man down for the rest of the match:

The equalizer did not come until the 79th minute, when Haris Tabakovic pulled the home team level:

90 minutes were not enough, and the two tired sides headed to extra time. But even that additional time could not decide matters, and the teams settled for the penalty shootout.

Perhaps the best chance in extra time was this from Italy, which Bosnia and Herzegovina keeper Nikola Vasilj turned aside:

The home team was up first, and Benjamin Tahirovic converted to give Bosnia and Herzegovina the early advantage:

Pio Esposito, who came on for Kean, sent his attempt — the first for Italy — over the bar:

Bosnia and Herzegovina converted their next two chances, taking an early 3-1 advantage in the shootout. That’s when Bryan Cristante stepped to the spot, only to find the woodwork:

That set the stage for Bajraktarevic’s winner.

For Bosnia and Herzegovina, this is their first World Cup since 2014, and they will slot into Group B along with Canada, Qatar, and Switzerland. For the side ranked 66th in the world, they will be the lowest-ranked team in their group.

Not that that matters much at the moment.

As for Italy, it will be yet another long four years of waiting, and hoping.