Torino stunned Milan to reach the Coppa Italia quarter-finals with a remarkable extra-time win at San Siro on Wednesday, Michel Adopo scoring the only goal to fire the 10-man visitors through.
A much-changed Milan side produced a disjointed display, struggling to break Torino down even after Koffi Djidji received his second booking with 20 minutes remaining in normal time.
After Vanja Milinkovic-Savic kept the Rossoneri at bay with a series of fine saves, Adopo capped a rapid break by converting Brian Bayeye's squared pass to snatch victory with a penalty shoot-out looming.
The result represents another setback for Stefano Pioli's men following Sunday's capitulation against Roma, ensuring Milan's wait for Coppa Italia glory will stretch to at least 21 years.
Torino squandered the first clear chance when Sasa Lukic was played through on goal 12 minutes in, with Ciprian Tatarusanu rushing out to save with his right leg.
Charles De Ketelaere twice went close to giving Milan the lead before the break, seeing his looping header hit the inside of the right-hand post prior to Milinkovic-Savic pushing his long-range effort away on the stroke of half-time.
With Torino continuing to stand firm, Milan's introduction of Junior Messias put them on top as he invited a clumsy challenge from Djidji, who was deservedly shown his second yellow card.
Milinkovic-Savic turned Theo Hernandez's powerful volley away in stoppage time as Torino held on to force an extra half-hour, in which the Serbia goalkeeper made a close-range stop to deny Olivier Giroud.
As Milan began to run out of ideas, they were hit with a sucker punch just six minutes out from penalties, Adopo tapping in Bayeye's low cross to stun San Siro into silence.
What does it mean? More cup woe for Rossoneri
Given Milan have won the Scudetto 19 times – a tally only bettered by Juventus (36) – it seems remarkable to think they have not lifted Italy's domestic cup since 2003.
While Torino's bid for a sixth Coppa Italia triumph continues, Milan's chances of adding to their five are over – Andriy Shevchenko, Rivaldo and Filippo Inzaghi were among the final goalscorers when they last won this competition.
While Adopo may have been the hero for Torino, his dramatic intervention was only made possible by Milinkovic-Savic, who kept Milan at bay with eight saves throughout the match.
The Serbia international had more touches (85) and passes attempted (63) than any other Torino player, demonstrating the pattern of the game, but he stood firm to emerge with a vital clean sheet.
De Ketelaere misses his chance
Big things were expected of De Ketelaere when he swapped Club Brugge for San Siro in August, but the Belgium international has struggled, failing to net a single Serie A goal for the champions.
Handed a start here, the 21-year-old went close twice in the early stages before fading, with Milan's only two clear chances falling to Giroud and Messias following their introductions from the bench.
Milan travel to Lecce for their next Serie A fixture on Saturday, while Torino host Spezia one day later.