Vincenzo Italiano says Fiorentina "really believed we could have a different ending", after La Viola suffered Europa Conference League final heartbreak for the second year running.
Italiano's side were beaten by West Ham in last year's showpiece, with Jarrod Bowen snatching a last-gasp winner in Prague.
Fiorentina suffered a similar fate 12 months later, as Ayoub El Kaabi struck four minutes before the end of extra time to give Olympiacos their first title in a major European competition.
La Viola embarked on a club record 13-match unbeaten run to reach their second successive Europa Conference League final.
But Italiano, who will depart the club at the end of the season, admitted it counted for nothing, with his side once again left to wonder what might have been.
"We really believed this time. It hurts," he told Sky Sports Italia. "It's disappointing for the second time.
"It's disappointing because again we had many situations to score goals, but the players did everything they could. It hurts to see my players cry. We really believed this time we could have a different epilogue to this campaign.
"Losing hurts; going all the way for two years running is something good, but naturally you have to lift a trophy, and we didn't manage it.
"The journey feels ruined when you have to watch the others lift the silverware. At this moment, I feel too bitter, disappointed, let down, because I really believed we could have a different ending."