Milan slumped to a second Audi Cup defeat in as many days with a 2-0 defeat to Premier League side Tottenham Hotspur.
The Rossoneri enjoyed moments of promise at Allianz Arena, but are left to lick their wounds once more after again failing to find the net.
In their second and final game of the pre-season tournament held in Germany, Coach Sinisa Mihajlovic made 11 changes to the side that lost 3-0 to hosts Bayern Munich yesterday.
Having been comprehensively beaten by the German champions, things did not get off to a good start for the San Siro club here either.
Just eight minutes had passed when Spurs forward Nacer Chadli, in for Harry Kane, unleashed a fierce strike from the edge of the penalty area following a corner to give the English side the lead.
It capped an opening period in which the North Londoners were the better of the two teams, but Milan had chances to equalise through Alessandro Matri and Suso.
At the other end, Rossoneri goalkeeper Christian Abbiati did well to foil Tom Carroll from doubling Spurs’ lead, but it remained 1-0 at the interval.
Mihajlovic made three changes for the start of the second half and 11 in total, with Colombian forward Carlos Bacca sending a header narrowly wide of Hugo Lloris’ post.
Carroll, however, was not to be denied and he added Spurs’ second on 71 minutes, curling home a neat finish from close range.
The Rossoneri tried in vain to force their way back into the contest but failed to seriously test Lloris as Spurs closed out a comfortable win.
Tottenham 2 – 0 Milan
Chadli 8 (T), Carroll 71 (T)
Tottenham Hotspur:McGee (Lloris 55); Trippier, Fazio, Vertonghen (Wimmer 46), Davies; Dier (Winks 55), Bentaleb (Alli 69); Onomah, Lamela (Dembele), Carroll; Chadli (Mason 55)
Milan:Abbiati (Donnarumma 46); Abate (De Sciglio 70), Alex (Paletta 46), Mexes (Ely 77), Calabria (Antonelli 77); Poli (Nocerino 46), Montolivo (De Jong 42), Jose Mauri (Bonaventura 77); Suso (Honda 77); Cerci (Luiz Adriano 78), Matri (Bacca 61)