Luka Modrić became the oldest scorer in a men's European Championship on Monday but has probably played his final game at a major tournament.
The 38-year-and-289-days-old playmaker missed a penalty against Italy in the 54th minute, but scored just a minute later to break the record held by Austria's Ivica Vastic (38 years, 257 days) from Euro 2008.
It looked like the 2018 World Cup runners-up and 2022 third-placed team had done enough for the last 16, but the holders levelled for 1-1 deep into injury time thanks to Mattia Zaccagni.
That sent Italy through as Group B's second-placed side while Croatia and Modrić are now clutching at straws.
"I don't know what to tell you, football is sometimes cruel. It has been shown again," Modrić told a news conference.
"We didn't deserve to concede this goal. We didn't doubt the fans, we knew they were always with us, thank you. We're sorry that it wasn't that victory to go to the next round."
With just two points, Croatia need Slovenia or Denmark to lose heavily on Tuesday and hope results in Group F go their way on Wednesday so they can finish as one of the four best third-placed teams.
Since the Euros were extended to 24 teams in 2016, no side with two points has progressed to the knock-out stages.
After also conceding late in the 2-2 draw with Albania, having opened the tournament with a 3-0 loss to group winners Spain, Croatia coach Zlatko Dalić was philosophical.
"Last minute Albania, last minute today. I can only congratulate the guys on the fight, the willingness, the sacrifice they showed. But here it is, it's not our tournament," he said.
Modrić, one of the most feted players of his generation, has extended his contract with Real Madrid for another season. But the chances of him turning out for Croatia at the 2026 World Cup look as remote as their chances of reaching the last 16 this week.