Chelsea vs AC Milan: The First Real Test of Xabi Alonso's Era

Chelsea’s pre-season has shifted tone. The early breeze of comfortable wins has given way to something more searching, more serious, as Xabi Alonso’s side hit Jakarta for a meeting with AC Milan that suddenly feels like a temperature check rather than a tourist stop.

Three straight victories over Crawley, Bromley and Western Sydney Wanderers had painted a smooth picture of life under the new manager. Then came the sting. A stoppage-time defeat to 10-man Tottenham in Australia, followed by a 1-0 loss to Juventus in Hong Kong on Wednesday, has stripped away any illusion that this summer would be simple.

Two weeks out from the Premier League kick-off, the margins start to matter.

Jakarta, Milan and a tightening clock

At Gelora Bung Karno Stadium this afternoon, Chelsea face a Milan side that offers a far sterner benchmark than most pre-season fare. The setting is exotic; the stakes are not. Alonso needs rhythm, clarity, a defensive structure that stops creaking whenever the opposition leans on it.

The schedule is brutal. AC Milan today in Indonesia, Johor Darul Ta'zim tomorrow in Malaysia. Two games in two countries in 24 hours. It forces rotation, but it also forces decisions. Who is trusted now, and who will have to wait?

This first fixture is expected to be the serious one. Near full-strength. Senior names. A side that looks something like the team Alonso wants to unleash on the Premier League in a fortnight.

Defence under the microscope

If there is a fault line in Chelsea’s pre-season so far, it runs straight through the back line. The structure has looked uncertain, the relationships loose. Alonso can point to the obvious caveat: he has barely had the chance to field a settled defence.

That is why Levi Colwill’s return matters so much. The England defender missed most of last season with an anterior cruciate ligament injury; Chelsea have felt that absence in both presence and personality. Colwill brings authority, a left-footed balance, and the chance to finally build some familiarity at the back.

He and Cole Palmer were both left out against Juventus on a poor pitch in Hong Kong, a precaution rather than a setback. The expectation is that both are available for minutes this weekend. How many, and in which game, will reveal plenty about Alonso’s risk appetite.

The No1 debate

There is another decision brewing behind that back four. Robert Sanchez returned from injury against Juventus, a welcome sight for a squad that craves stability in goal. Yet the story does not end there.

Mike Penders, the young Belgian, is pushing hard. He has been waiting, watching, and now senses a genuine opening in the battle for the No1 shirt. Pre-season is often where reputations are made or broken for goalkeepers; a single commanding performance against Milan could tilt the hierarchy.

Alonso must choose. Stick with the experience of Sanchez from the start in Jakarta, or lean into the future and hand Penders the gloves in a game that feels more like a dress rehearsal than a training exercise.

Mudryk in the shop window

The Juventus defeat in Hong Kong was decided by a thunderous second-half strike from Edon Zhegrova, but the night’s real focus lay elsewhere. Mykhailo Mudryk was back.

With his anti-doping disciplinary case with the FA now resolved, the Ukrainian winger has re-emerged into the spotlight, and not just for Chelsea. Several clubs are circling with loan interest, and every minute he plays now will be studied as closely by scouts as by Alonso’s staff.

He could be in line for his first Chelsea start since November 2024. The timing is intriguing. A strong showing against Milan might accelerate a move away; it might also remind Alonso of the raw, unpredictable weapon he has on his hands.

Youth staking a claim

For all the noise around results, pre-season is still about discovery, and Alonso has already unearthed one standout story: Mahdi Nicoll-Jazuli.

The 16-year-old midfielder, Sydney-born and representing England at youth level, was handed his first senior start against Juventus. Not as a token gesture, but in a key role alongside Moises Caicedo, and ahead of Romeo Lavia and Dario Essugo. That choice said plenty about how quickly he has impressed.

Nicoll-Jazuli played with a composure that belied his age. If he features again against Milan, it will be another sign that Alonso is serious about fast-tracking Cobham’s latest graduate into the real conversation.

On the flanks, Geovany Quenda has offered a different kind of promise. The 19-year-old winger, a £40million signing from Sporting, was one of the few bright sparks in an otherwise flat display against Juventus. Direct, fearless and sharp, he already looks ready to contribute now rather than later.

These are the small wins that matter in July and August. They don’t erase defeats, but they do shape the squad.

Rotation, risk and a looming season

With two games in two days, Alonso will have to split his resources. The logic is clear: go strong against AC Milan in Jakarta, then lean more heavily on squad and youth options against Johor Darul Ta'zim in Malaysia on Sunday.

That means today’s predicted XI carries weight. Penders in goal; a back four of Palestra, Fofana, Colwill and Hato; Lavia and Caicedo as the midfield platform; Estevao, Palmer and Mudryk behind Joao Pedro. On paper, that is close to full strength. On grass, it needs to look like it.

Results in pre-season are often talked up or talked down to suit the mood. Alonso will know better than to panic over two defeats. But he will also know that patterns matter, and that confidence is fragile when a new project is taking shape.

Jakarta offers a chance to steady the picture. To tighten the defence, to clarify the goalkeeping pecking order, to see if Mudryk, Palmer and the emerging kids can carry threat against elite opposition.

The clock is ticking. How quickly can Chelsea turn promise into something more concrete?