Bologna ended their 51-year-old waiting for silverware in a spectacular way in the stadio Olimpico when Lewis Ferguson raised the trophy in the Roman night sky after a Dan Ndoye Strike AC Milan sank.
The beaten finish of the winger early in the second half turned out to be decisive in a tense struggle and saw Captain Ferguson an iconic figure in the legendary history of the Rossoblu.
Bologna had paid tribute to their last trophy-winning side, the Coppa Italia champions from 1973-74, with a huge banner before the kick-off, and challenged the current team to make their memory come true.
They did exactly that with a controlled version in which they showed that little of the nerves that were expected on such a historical occasion.
It marked a dream climax for a difficult season for Ferguson, who had spent the year with fighting an ACL injury before he was disturbed by muscular problems.
The sensational success story of the midfielder born in Emilia-Romagna, however, hit new heights when he added a trophy to a list of awards that already contained a Serie A midfielder of the year, Champions League qualification and a club record points in total.
For Milan, the defeat was the last nightmare in a season, with the side of Sergio Conukicao potentially staring through the barrel at a year without European football after Bologna had demanded a Europa League spot with their victory.
Organizers had not cut the Cup-Laatste Praal, with a light show and tricolor fireworks on a fleeting appearance of trophy carrier Roberto Baggio before the kick-off.
Once the whistle blew, the game turned out to be just as lively as the pre-match entertainment, Alex Jimenez threatening for Milan early before Ferguson curled a shot and a Santiago Castro Captro Ating Header Test Mike Maignan.
Cat-like reflexes from Bologna goalkeeper Lukas Skorupski held a breathless level of game in the 10th minute when he made two point-blank rescues before the ball was brought to safety.
From there the game finally established, Ferguson saw a lot of the ball when Bologna dictated and Milan who wanted to hit the break.
The Scot was at the end of half when a poorly timed challenge on Rafael Leao gave him a booking and a bloody nose of catching a lost boot.
What Vincenzo Italiano also said to his players during the break, it clearly had an effect, because an upheld Bologna took the lead for five minutes in the second half.
Switzerland International Ndoye got stuck to a loose ball in the box after Riccardo Orsolini had been tackled, entering a finish for the traveling Rossoblu fans.
The Subs soon started rolling further, Conukicao made a triple change by introducing Kyle Walker, Joao Felix and Santiago Gimenez in one go in the hope of a spark, while Italiano responded by switching to a more conservative back three.
The changes only produced an impasse that suited Bologna perfectly with Bologna, where Gimenez had one attempt that found the arms of Skorupski, while Ndoye threatened on the other side again.
When the whistle finally blew, it was euphoria for the underdogs, because the long-suffering Bologna fans celebrated a night that will be remembered for generations.