Mario Pasalic scored the winning penalty as AC Milan lifted the Supercoppa Italiana for the first time in five years with a 4-3 shootout victory over holders Juventus in Doha.
The Chelsea loanee kept his nerve to find the top left corner with Milan's fifth spot-kick after their 17-year-old goalkeeper Gianluigi Donnarumma had denied Paulo Dybala.
Giorgio Chiellini volleyed Juve into an 18th-minute lead at the Jassim Bin Hamad Stadium but Giacomo Bonaventura headed Milan level seven minutes before the break to leave the game level at 1-1 after extra-time.
The result means Milan have now equalled the Turin club's record of seven super cup wins.
It was the ninth time the competition had been played outside of Italy and Massimiliano Allegri's Juve were strong favourites ahead of the clash.
The Serie A champions -- and current leaders -- began brightly and Croatia international striker Mario Mandzukic was the first to threaten when his half-volley was tipped around the left upright by Donnarumma.
Stefano Sturaro should have opened the scoring in the 17th minute but, after being played in by Gonzalo Higuain, the midfielder's effort lacked power and was repelled by the Milan keeper before the ball was scrambled behind by Ignazio Abate.
Juve did not have to wait long for another opportunity, though, and from the resultant corner Chiellini powerfully connected with Miralem Pjanic's delivery to claim his first goal since a brace against Sampdoria in October.
Milan, who qualified for the final as runners-up to Juve in last season's Coppa Italia, had struggled up until that point but they gradually grew into the game as their opponents failed to build on the early breakthrough.
Slovakian midfielder Juraj Kucka had a header comfortably saved by Juve keeper Gianluigi Buffon nine minutes prior to the interval, before parity was restored two minutes later.
Creative midfielder Suso found space on the right to curl in a dangerous left-footed cross and Bonaventura timed his run perfectly to flick the ball past Buffon and into the far corner.
The equaliser seemed to increase the confidence of the Rossoneri and 12 minutes after the restart they almost turned the game around.
Spaniard Suso was once again the provider as his ball from the right was headed towards goal by defender Alessio Romagnoli before cannoning back off Buffon's crossbar.
Sami Khedira then forced Donnarumma into a fine save at the other end, before Bianconeri substitute Dybala, a 67th-minute replacement for Pjanic, flashed a shot just off target.
Milan, who last lifted the trophy in 2011 when Allegri was their manager, came close to snatching a late winner in normal time when another Suso delivery was nodded down into the ground by Carlos Bacca before being beaten away by Buffon on the line.
Colombian striker Bacca then wasted a fantastic opportunity two minutes into extra-time as he miscontrolled the ball with the goal gaping after Buffon had saved the initial attempt.
Juve full-back Patrice Evra thought he had claimed the winner in the 111th minute but he was correctly flagged offside, before Dybala blazed over from eight yards to leave the game requiring penalties.
Gianluca Lapadula missed Milan's first kick but, after Mandzukic hit the bar and Dybala saw his effort saved, substitute Pasalic stepped up to give Vincenzo Montella's men victory.