Manchester United won their opening International Champions Cup game after regulation time ended 1-1 and 26 spot kicks were required to finally separate the two sides in the ensuing penalty shootout. Milan’s Franck Kessie missed the final and decisive effort from 12 yards but José Mourinho’s team again struggled for fluency, with Alexis Sánchez a class above his team-mates once more.

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The Chilean starred in the drab goalless affair with San Jose Earthquakes and was again United’s one bright light at the StubHub Center. Mourinho spent a muggy evening in south Los Angeles frustrated with his side’s display, his body language around the technical area leaving no doubt regarding his feeling. There was, in truth, only the odd flash of invention and when it appeared Sánchez was usually involved.

Juan Mata forced an opening corner from a free-kick after United’s captain for the evening, Matteo Darmian, was felled. It came to nothing but when Scott McTominay drilled a shot at Gianluigi Donnarumma’s goal from the right the No 1 needed to be sharp to save low. The keeper did precisely the same later on when Sanchez pinged a 30-yard free-kick from the left to draw “oohs” from a not-quite full stadium.

The next time United threatened there were cheers to hail arguably their finest move of the tour. Mata hit a slick first-time pass through to Sánchez and the Chilean beat Donnarumma to his left with a classy finish.

When the team sheet dropped the absence of Anthony Martial had meant some intrigue regarding who Mourinho might select at No 9. The Frenchman had earlier flown home and out of the tour in abrupt fashion to attend the birth of his child. There had been no warning he might depart – Mourinho did not mention the prospect at UCLA last week when branding pre-season “very bad” due to the number of players absent due to post-World Cup holidays.

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The manager’s answer to Martial’s departure was to name Sánchez at centre-forward, with Mata and McTominay as two in support in what was a rare 3-4-2-1 shape. The three centre-back system did nothing to stop Suso’s equaliser, which arrived moments after Sánchez’s strike. Leonardo Bonucci threaded a long pass into the Spaniard and he beat Lee Grant confidently. An annoyed Mourinho waved a hand before his face, a gesture to coaching staff to indicate a concentration deficit in defence.

With Antonio Valencia’s tour also over due to a calf injury and Nemanja Matic not yet match fit Mourinho had named the strongest side possible, with Andreas Pereira, Grant and Axel Tuanzebe the only fringe players. Valencia’s absence may hand Darmian a chance to start the season at right-back and this may have been behind him being given the armband.

The Italian looked sharp as did Sánchez – one reverse pass to Luke Shaw bamboozled Milan’s rear-guard. Later, the same pair were involved when United turned defence into attack. A Shaw burst from near the area carried the ball before he fed Sánchez. The No 7 raced in on Milan’s goal, found Ander Herrera, and after his first shot was beaten out the follow-up effort was miscued.

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At a “mandatory hydration break” just after the half hour mark, Mourinho seemed to remonstrate with Tuanzebe, perhaps regarding Milan’s strike, and there was also a word for Shaw and Grant. Played resumed and when the break neared the manager had seen enough, taking one of his trademark wanders off early ahead of the whistle for the interval.

Within seconds of the second half starting Sánchez supplied some stardust. He hit a dipping cross-field ball from the left to Darmian. As the right-back roved down his wing Sánchez ran to the edge of the area and performed a scissor-kick that was spectacular but off target.

From there the contest sagged for a passage until Milan spun United too easily, Tuanzebe was left stranded, and Patrick Cutrone could shoot. Cue an exasperated Mourinho turning to his bench once more to complain at what he witnessed.

United finally managed an attack via Shaw. His cross went for a corner on the right and when the delivery came to him his shot was saved to the left by Pep Reina, who had just replaced Donnarumma. At the close Nikola Kalinić, a Milan replacement, saw his effort rebound back off Pereira’s right post, leaving the contest to be settled by the marathon shootout.

Manchester United (3-4-2-1): Grant (Pereira J); Smalling, Bailly, Tuanzebe; Darmian, Herrera, Pereira A, Shaw (Fosu-Mensah, 75); McTominay, Mata; Sánchez

AC Milan (4-3-3): Donnarumma; Abate, Musacchio, Bonucci, Calabria; Kessie, Locatelli, Bertolacci; Suso, Cutrone, Calhanoglu

Referee: Baldomero Toledo

Booked: Herrera (90)

Attendance: 21,742