Missing out on the 2018 World Cup signals the end of an era for the Italy national team as a number of veteran stars announced their retirements following Monday's 1-0 aggregate defeat to Sweden.
Legendary goalkeeper Gianluigi Buffon was among those calling time on their international career.
"It's a shame my last official game coincided with the failure to qualify for the World Cup," Buffon said, per BBC Sport.
AS Roma midfielder Daniele De Rossi offered a more definitive statement about his national team future.
"My adventure here ends," he said, according to Roma's English language Twitter account. "It's sad to think this was the last time I will wear these colours. But I couldn't be more proud of the journey, everyone I've played alongside."
Football Italia passed along comments from Juventus defender Andrea Barzagli, who told Rai Sport his international career is over:
"In football terms, it's the biggest disappointment of my life. The Italy side gives you unique sensations. It gives you goosebumps, creates friendships between all the Italy fans, they are finally united. It's a real shame to end like this. ... I don't know what we missed, all I know is we're out of the World Cup, it's a unique disappointment and leaving this group of lads is painful."
The retirements of Buffon, De Rossi and Barzagli will hit hard because all three players were a part of the 2006 side that won the World Cup. Chiellini missed out on the 2006 World Cup but helped Italy finish runners-up at the 2012 European Championship.
The circumstances behind the mass exodus will be painful for all involved, but missing out on the 2018 World Cup hastened the inevitable for the four players since their international careers were unlikely to extend much beyond the tournament.
Buffon will turn 40 in January. Barzagli, De Rossi and Chiellini are 36, 34 and 33 years old, respectively.
Slowly but surely, Italy have lost the stars responsible for delivering their fourth World Cup. After Monday night, it will be up to a new generation to put the Azzurri back on top of the football world.