Italy failed to reach the FIFA World Cup for the first time since 1958, losing 1-0 on aggregate to Sweden in a two-legged play-off.
Jakob Johansson scored the winner in the first leg and the Italians were unable to break through a resolute Swedish defence at the San Siro on Monday night.
The Italian players were distraught - Gianluigi Buffon, Andrea Barzagli and Daniel De Rossi all announced their retirement from international football soon after the final whistle.
Buffon was in tears as he gave his post-match interview on the pitch.
“I'm not sorry for myself but all of Italian football,” the 39-year-old Juventus legend said in an emotional post-match interview.
“We failed at something which also means something on a social level. There's regret at finishing like that, not because time passes.
“There is certainly a future for Italian football, as we have pride, ability, determination and after bad tumbles, we always find a way to get back on our feet."
Buffon was praised earlier in the evening for applauding the Swedish national anthem whilst boos rang out in the famous stadium in Milan.
Swedish fans sing to the Italians
The travelling Swedish support were quite understandably having a whale of a time whilst the Italians began to prepare for life without a World Cup.
Most Italian football fans have never experienced watching the international tournament without being able to cheer on their nation.
The Swedish fans in the San Siro had a message to the Italian fans - and sang it loud and clear in the stands.
"Always look on the bright side of life."
The Scandinavian supporters were surely far from impressed with the Italian support booing their national anthem ahead of kick-off - this was definitely the best way to respond!
Janne Andersson's Sweden will be in pot three when the World Cup draw takes place on December 1 in Moscow.