Andre Silva was the star with a brace as Milan made short work of Shkendija, crushing them 6-0 in the first leg of the Europa League play-off.
Riccardo Montolivo (with a double of his own), Fabio Borini and Luca Antonelli rounded out the scoreline of a dominant performance.
The Rossoneri already got through one preliminary round, beating Craiova 3-0 on aggregate, but Leonardo Bonucci made his competitive debut with the captain’s armband. Lucas Biglia and Alessio Romagnoli were injured, with M’Baye Niang, Gustavo Gomez, Davide Calabria, Gabriel Paletta and Jose Sosa left out. Macedonians Shkendija also wear red and black, but changed to their white away kit in front of 40,000 at San Siro.
Antonelli’s glancing header whistled wide and Franck Kessie struck the side-netting, but Andre Silva broke the deadlock when he pounced on a loose ball from 15 yards to drill into the bottom corner. It was the Portugal international’s first goal at San Siro.
Shkendija had their first chance after 22 minutes with Besart Abdurahimi’s half-volley over the bar, but the Rossoneri doubled their advantage with an unexpected scorer.
Kostadin Zahov meekly flapped at a Suso free kick and Montolivo, stripped of the captain’s armband by newcomer Bonucci, was quickest to react and tap in. He hadn’t found the net for the Rossoneri since April 2014.
Soon after, Andre Silva completed his brace thanks to a goal of sheer determination. He controlled the ball with his back to goal, turned one defender, rode another tackle and prodded past the on-rushing goalkeeper. Silva became the first Milan Number 9 to bag a European brace at San Siro since Pippo Inzaghi in a 2-2 draw with Real Madrid in April 2010.
Hakan Calhanoglu fired over, but Blagoja Todorovski remained dangerous down the Shkendija right, his cross-shot just missing two teammates.
Kessie continually bombed forward, twice just failing to get the final touch to a cross from a couple of yards out. On the stroke of half-time, Zahov stuck out a foot to deny Suso’s fierce angled drive.
Straight after the restart, Andre Silva was about to complete his hat-trick, but tapped on to the upright from a corner and Zahov flapped the rebound off the line.
Calhanoglu and Luca Antonelli blasted just off target, but Besart Ibraimi had two efforts deflected wide.
Milan did add a fourth, as Andre Silva scuffed a give-and-go with Andrea Conti, but it accidentally turned into an assist for Borini to tap in.
Moments later, Suso’s wayward shot got past Zahov and found Antonelli totally unmarked at the far post.
Andre Silva thought he’d completed his hat-trick with an audacious back-heel flick from five yards, but was denied by a desperate save.
There was still time for young striker Patrick Cutrone to clip the upright from close range and the truly improbable Montolivo completing his brace, given too much time to turn and score from just inside the area.
At the 89th minute, Jack Bonaventura walked off to the locker room with a recurring groin injury, as all the substitutions had been completed.
Milan 6-0 Shkendija
Andre Silva 13, 27 (M), Montolivo 25, 86 (M), Borini 67 (M), Antonelli 69 (M)
Milan: G Donnarumma; Conti (Abate 69), Bonucci, Zapata, Antonelli; Kessie, Montolivo, Calhanoglu (Bonaventura 60); Borini, Andre Silva, Suso (Cutrone 75)
Shkendija: Zahov; Todorovski, Bejtulai, Cuculi, Celikovic (Teqja 64); Alimi, Totre; Radeski, Hasani, Abdurahimi (Bojku 70); Ibraimi
Ref: Lechner (AUT)