Xabi Alonso Aims for First Chelsea Win Against AC Milan in Jakarta

The Xabi Alonso era at Chelsea is barely underway, but the demands are already clear. After back-to-back pre-season defeats, the new manager steps into Jakarta on Saturday needing more than just improved fitness numbers. He needs a performance that looks like a plan.

Across the halfway line, AC Milan arrive with exactly that: clarity, momentum and an unbeaten pre-season under Ruben Amorim, the former Manchester United target now charged with reshaping the Rossoneri at San Siro.

A heavyweight meeting far from home

Chelsea vs AC Milan in Indonesia sounds like a marketing department’s dream, but for both coaches it cuts a little deeper.

Alonso is still searching for his first real tune from a Chelsea side that slipped to a 1-0 defeat against Juventus on Wednesday. The patterns were patchy, the finishing blunt, and the familiar questions about identity resurfaced quickly.

Milan, by contrast, have used the summer to build quietly but steadily. Their last outing, a 1-1 draw with fierce rivals Inter, underlined both their resilience and the early imprint of Amorim’s ideas. Sunday’s clash in Jakarta is their final friendly before the real grind begins, and the Portuguese coach knows an unbeaten pre-season would be a powerful message to his new dressing room.

A win over Chelsea would do more than decorate the fixture list. It would close Milan’s summer with a statement.

Chelsea’s new faces, and one long-awaited return

Chelsea’s recruitment has already turned heads, but not all of the club’s big moves will be on display in Jakarta.

The $155 million signing Morgan Rogers will not feature, the England attacker still on an extended break after the World Cup. His absence strips away one obvious source of attacking flair, leaving Alonso to lean more heavily on the options he already has in the camp.

Danny Welbeck, though, is available and under the spotlight. The surprise signing made his debut in the loss to Juventus, and this match offers another chance for the veteran forward to sharpen his edge and show he can be more than a short-term stopgap. His movement, link play and experience could be vital as Alonso tries to stitch together a more coherent attacking structure.

Then there is Mykhailo Mudryk, whose story adds a different kind of intrigue.

The Ukrainian winger came off the bench for just eight minutes against Juve, his first appearance for Chelsea in almost two years. His career was derailed in 2024 after he tested positive for the banned substance meldonium, a case that left his future in limbo until he was cleared of the remaining ban on appeal.

Now he is back, desperate for rhythm, relevance and trust. Jakarta might only offer him another short burst of minutes, but every touch will be watched closely. For Alonso, unlocking Mudryk’s pace and directness could transform Chelsea’s threat on the break.

Amorim’s Milan eye the perfect pre-season

On the Milan side, the mood is different. Not relaxed, but assured.

The draw with Inter showed Amorim’s side can grind when needed, and the broader pre-season run has been defined by control and organisation rather than chaos. This is a team that has not tasted defeat in its summer schedule, and the players know one more solid display will send them into the new campaign with belief to spare.

Amorim is looking for a reset at San Siro. His methods are built on structure, intensity and clear roles. A polished display against Chelsea would not just cap an unbeaten pre-season; it would reinforce the sense that Milan are ready to hit the ground running when competitive football returns.

Stakes higher than the label “friendly” suggests

On paper, it is only a friendly in August. No trophies, no league points, no lasting consequences.

But managers read these games differently.

For Alonso, this is about proof of progress. Can Chelsea control spells of the game? Can they press as a unit? Can the attack finally knit together without their marquee forward signing on the pitch? Another disjointed display would not define his tenure, but it would deepen the sense that the rebuild will be slower and more painful than hoped.

For Amorim, the challenge is to protect the standards Milan have set across pre-season. The unbeaten run is not a prize in itself, but it has become a reference point. End it with a limp performance, and questions creep in. Extend it against a club of Chelsea’s stature, and the squad heads into the new season with their chests out.

Jakarta will feel the heat in more ways than one. Two European giants, two new managers, two very different kinds of pressure.

One chasing a spark. The other trying to bottle momentum before the real battles begin.