Gianluigi Donnarumma saved the decisive penalty from Paulo Dybala as AC Milan won the Supercoppa Italiana 4-3 on penalties after a 1-1 draw with Juventus in Doha.
Mario Pasalic sealed victory for Milan after Donnarumma had spurned Dybala, who also missed a gilt-edged extra-time chance.
Juve's Mario Mandzukic also missed from 12 yards, with Gianluca Lapadula reprieved having failed to convert for Milan.
Alessio Romagnoli hit the bar for Milan as Vincenzo Montella's men shaded the second half, before having to withstand heavy Juve pressure as 30 minutes of extra time failed to produce a winner.
The win on penalties mean Milan now join Juve in having won the trophy a record seven times, with Montella claiming his first silverware with the Rossoneri.
Massimiliano Allegri's men, meanwhile, have appeared in five straight editions of the Supercoppa, winning three – but losing on the two occasions it has been played in Qatar.
Juve had made a strong start to the match, with Mandzukic and Stefano Sturaro testing Donnarumma, but the teenage goalkeeper was helpless to prevent Chiellini's flicked header from a Miralem Pjanic corner flying beyond him.
Allegri's men were in control, but they lost Alex Sandro through injury and suffered more frustration when Milan moved level after 38 minutes.
Milan almost completed the comeback early in the second half, Romagnoli's deft header hitting the bar from another brilliant Suso delivery.
A thrilling Supercoppa continued with Donnarumma making a superb save from Sami Khedira's 20-yard drive at the other end after Gonzalo Higuain had created the opportunity.
Milan's main chances were coming in the air and Carlos Bacca had an aerial effort beaten away by Buffon, with in-form Suso again the creator.
Dybala missed the best chance of the additional period, blazing over from Evra's cross before the Juve defender was fuming at another failed penalty appeal – this time for a Mattia De Sciglio handball - as the match moved to spot-kicks.
