In a match that served as a curtain-raiser for Milan’s 2025 pre-season tour, Christian Pulisic’s side went head-to-head with Arsenal in Singapore. It was a competitive outing that ended in a 1-0 defeat for the Rossoneri, yet what followed after full-time left many scratching their heads: a full penalty shootout.
It wasn’t due to a draw, and it had nothing to do with any official tournament rules. So why did it happen? The answer might not be what fans expect.
Under the lights at Singapore National Stadium, Massimiliano Allegri led Milan for the first time since his dramatic return to the club. His debut saw a new tactical setup featuring a three-man defense comprised of Fikayo Tomori, Malick Thiaw, and Strahinja Pavlovic. At the top end of the formation, Rafael Leao and Christian Pulisic formed the attacking duo.
Arsenal dominated possession for much of the game, and Bukayo Saka’s second-half strike proved enough to hand the Gunners victory. Milan had their moments, particularly through Pulisic, who showed glimpses of sharpness in the first half, but the Rossoneri struggled to produce clear-cut chances.
Pulisic’s performance and Milan’s attacking void
While the scoreline will disappoint, the friendly also offered early insight into how Pulisic might be utilized under Allegri. With Santiago Gimenez unavailable for the pre-season and Lorenzo Colombo, the only center-forward, likely on his way out, Pulisic often dropped deep, helping Samuele Ricci in the build-up. Though he only played the first half, the American’s movement and sharpness hinted at a key role in the months to come.
But despite these tactical experiments, the headline-grabbing moment came after the final whistle.
The reason for the post-match penalty shootout
Though Arsenal had already claimed victory, fans inside the stadium were surprised to see both teams return for a penalty shootout. It was not a draw, nor a tournament rule — and Milan ultimately “won” the shootout 6-5 after goalkeeper Lorenzo Torriani saved three penalties, including efforts from Martin Odegaard, Jakub Kiwior, and Reiss Nelson.
So, why did the teams do it?
As it turns out, the penalty shootout had nothing to do with the outcome of the match. It was a pre-arranged spectacle, designed purely for fan entertainment. There was a complete match and a shootout that had been planned beforehand. Apparently, the subsequent penalty shootout was purely for the enjoyment of the spectators, and it had nothing to do with the outcome of the friendly match.
This approach is becoming more common during preseason tours, particularly in regions like Asia and the United States, where clubs want to maximize engagement with international fanbases. Friendly shootouts offer supporters the thrill of high-stakes moments without any competitive consequences.
