Sensational goals from Kevin-Prince Boateng and Clarence Seedorf gave Milan the Trofeo Berlusconi, beating Juventus 2-1.
Mirko Vucinic got one back as the Bianconeri improved considerably in the second half, but the home side lost several players to injury.
The traditional pre-season match at San Siro saw Andrea Pirlo return to face his former teammates for the first time since ending his 10-year stay with the Rossoneri.
Antonio Cassano was the only available striker, as Alexandre Pato and Robinho return from Brazil on Tuesday, while Zlatan Ibrahimovic, Pippo Inzaghi and Stephan El Shaarawy are injured.
Boateng was playing in a more advanced role and made full use of it, opening the scoring with a spectacular volley after nine minutes. Ignazio Abate's cross came in from the right and he managed to keep his right-foot volley low into the far bottom corner past Gigi Buffon.
A smart Cassano through ball released Gennaro Gattuso, but he lost his footing under pressure.
Seedorf made it 2-0 with a perfect right-foot free kick, curled round the wall and in off the inside of the far post with Buffon rooted to the spot.
Juventus finally got a genuine scoring opportunity after 28 minutes with a Claudio Marchisio screamer that swerved round Christian Abbiati only to crack against the upright.
Boateng limped off with a knee problem and made way for Mathieu Flamini, moving Seedorf and Urby Emanuelson to more advanced positions. Alessandro Matri also picked up a knock to be replaced by Alex Del Piero.
Within 30 seconds of the restart, Taye Taiwo sprained his ankle and made way for Gianluca Zambrotta. Abbiati beat away a swerving Pirlo snapshot from distance.
Juventus got back into it when Del Piero threaded through for Mirko Vucinic's angled drive with the outside of his right foot.
Another Vucinic attempt was charged down in the box, while Abbiati stuck out a leg to parry from Del Piero. Juve piled on the pressure, but Milan had penalty appeals when Flamini's shot was charged down by a hand.
Teenage striker Kinglsey Boateng no relation to Kevin-Prince unleashed a curler that shocked Buffon and thumped the far top post in the final minutes. Cassano then forced Buffon into a crucial save with his outstretched foot.
Milan 2-1 Juventus
Scorers: K-P Boateng 9 (M), Seedorf 22 (M), Vucinic 57 (J)
Milan: Abbiati; Abate (Oddo 89), Nesta (Rodrigo 57), Bonera, Taiwo (Zambrotta 48); Gattuso (K Boateng 66), Ambrosini, Seedorf (Antonini 85); Emanuelson, K-P Boateng (Flamini 30); Cassano
Juventus: Buffon; Lichtsteiner, Barzagli, Chiellini, De Ceglie (Ziegler 85); Pirlo, Marchisio (Pazienza 73); Krasic (Quagliarella 85), Vucinic, Matri (Del Piero 43), Vidal (Pasquato 54)
Betting on Serie A? Bet365 are offering a 100% deposit bonus, up to £200 - find out more