Teenage goalkeeper Antonio Donnarumma and big-money Milan signing Carlos Bacca missed penalties as Real Madrid won the International Champions Cup with a 10-9 victory in a marathon shootout in Shanghai.
Real thrashed Manchester City 4-1 to win the International Champions Cup Australia last week and lifted the China version of the tournament on Thursday to end their pre-season tour unbeaten.
There was no separating the two sides in 90 minutes, with the impressive Kiko Casilla twice denying Milan new boy Bacca - who came on at half-time - in the second half with fine saves.
It was left to spot-kicks to decide the winner of the trophy and it was Real who came out on top, with Bacca and 16-year-old Donnarumma failing to hold their nerve.
Donnarumma had denied Toni Kroos to extend the shootout, but he went from hero to villain and both sides will now head to Munich to take part in the Audi Cup next week.
Rafael Benitez included Luka Modric and Karim Benzema in his starting line-up after the duo missed Monday's 3-0 victory over Inter due to niggles, while Sergio Ramos - reportedly set to sign a new contract - dropped to the bench.
But Real lacked the attacking threat they posed in impressive wins against City and Inter and they were almost caught out by the pace of Milan striker M'Baye Niang five minutes before half-time.
The young French striker opted to go it alone when he lacked support and burst past two defenders before clattering into Keylor Navas after taking a heavy touch, which cost him the chance to get a shot away.
Benitez and Sinisa Mihajlovic made several changes at half-time, with Bacca and Luiz Adriano among the Milan players to enter the fray, while Ramos and Kroos were also brought on.
Kroos had a chance to open the scoring soon after, but his shot from the edge of the area deflected wide after good work from fellow substitute Jese Rodriguez.
Real looked far more dangerous after a poor first half display and Diego Lopez - facing his former club - kept out Cristiano Ronaldo's downward header after some lovely trickery and a precise cross from Isco.
Bacca almost opened his Milan account in spectacular fashion with a thunderous strike that was destined for the back of the net until Casilla denied him with an outstanding reflex save on the hour-mark.
Casilla thwarted the Colombia striker again when he surged into the penalty area and unleashed a well struck shot 10 minutes from time.
Bacca failed to find the back of the net once again in a shootout, but Kroos missed the chance to secure victory when Donnarumma kept out his spot-kick.
The young keeper was unable to find the back of the net himself, though, as Casilla's save ensured Real lifted another trophy.
