From the floodplain of the Thames six days ago to the bustling banks of the Naviglio Grande, match four of the Champions League group stage between Chelsea and AC Milan takes in another picturesque setting tonight.

Last week, seven Academy graduates were among the players leaving the Stamford Bridge pitch – one of them Fikayo Tomori, sporting the livery of the Rossoneri – after a group-changing three-goal success for the Blues.

On Saturday, Milan looked a different beast to the one bettered at Stamford Bridge, convincingly beating Juventus 2-0. The same day, though, Chelsea tamed Wolves with a second successive 3-0 scoreline – the first time the club has done that since autumn 2020.

As things stand Group E is the most tightly poised, just two points separating top and bottom. That could end up with teams tied on points and results in head-to-head coming into play, affecting both teams’ approach in the ‘return’ game tonight.

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You do not have to be on the roof of the Duomo to see this could be a cracker. Milan will be all out to banish the beating they received a week ago, while Chelsea hope to consign to history a poor recent record of five straight losses on Italian soil.

Chelsea team news

Graham Potter already looks to be navigating the Premier League-Champions League two-step with conviction, resting several likely starters in Milan for the win against Wolves.

Seven changes were made (mostly for rest and recovery reasons), yet there was the same fluency and progressive play that brought last Wednesday’s European victory. The Blues pounced on errors, found space in the box at set plays, overmanned and swamped our opponents at times.

It is a great sign when the goals are flowing at one end while being stifled at the other. The Blues had not managed successive clean-sheet victories across all competitions since February.

Lifelong Blues fan Armando Broja nailed his first goal for the first team and there was a sprightly debut run-out for attacking midfielder Carney Chukwuemeka.

The Blues’ marauding wing-backs, Player of the Match Reece James and Ben Chilwell, earned praise for their contribution last Wednesday. Four corners delivered in the first quarter of the game by the Londoners seemed to affect the initially aggressive Rossoneri and it was Chilly’s delivery that fell for Wes Fofana to open the scoring.

Both were heavily involved in the next two, Reece assisting the second and slamming in the third himself. They may experience closer attention this evening, though that is easier said than done. In the competition as a whole only Barcelona’s Ousmane Dembele has crossed more times from open play than James.

The Blues also restricted Milan’s well-regarded strikeforce to just four shots in London. In recent Champions League campaigns only Malmo in October 2021 (two) and Galatasaray in March 2014 (three) summoned fewer efforts against the Londoners.

Regular starters Pierre-Emerick Aubameyang (who has netted in his last starts), Chilwell, James, Thiago Silva and Raheem Sterling will likely be back on the teamsheet for this second head-to-head fixture. Following his unlucky injury Fofana will be out for a few more weeks, while N’Golo Kante and Hakim Ziyech have not travelled.

Pioli plots revenge

‘After a couple of minutes we tried to do things that weren’t part of our game,’ observed Milan coach Stefano Pioli at Stamford Bridge, ‘and our opponents were able to exploit the space in behind us, they were so quick.’

He will therefore welcome potential returns for first-choice left-back Theo Hernandez, who played in a big 2-0 weekend win against Juve, and right-winger Junior Messias, who will increase Milan’s threat level in wide areas compared to London.

The attacking Hernandez is vital to the execution of Stefano Pioli’s tactical plan, while Messias’s qualities are closer to those of the still-absent Alexis Saelemaekers. However Charles De Ketelaere has joined the list of wounded.

And against Juve, midfield general Ismael Bennacer (who had Ruben Loftus-Cheek competing against him closely in the Stamford Bridge game) showed how he can break up play and set the metronome of the game. Pioli also rotated, with less-used Matteo Gabbia alongside Fikayo Tomori in central defence and Tommaso Pobega replacing Charles De Ketelaere in midfield in a fluid 4-3-3 formation that allowed his players to man-mark the visitors’ danger men.

San Siro buzzed expectantly whenever the ball went out to the left wing for Rafael Leao, but it was Tomori, paying back for his lapse at the Bridge, and Brahim Diaz, taking on opponents from right wing, who scored the goals. This was their second clean-sheet win of the season.

Pioli praised his team’s energy, intensity and determination despite the continued absence of regular starters including keeper Mike Maignan, centre-back Simon Kjaer, right-back Davide Calabria, attacking midfielder Alexis Saelemaekers and veteran striker Zlatan Ibrahimovic. None are back tonight.

We have history

San Siro figured large among Blues fans’ dream trips long before the maiden Champions League campaign in 1999/00 took us there. The 1-1 group stage draw there in late October – especially Dennis Wise’s equaliser from substitute Robbie Di Matteo’s diagonal pass – was instantly immortalised for the Chelsea songbook.

Back then, despite a draw and a defeat in the opening two games (ring any bells?), the Londoners eventually qualified for the second group stage by beating Hertha Berlin at the Bridge.

Milan have lost four of their last five matches when hosting Premier League clubs. This is our fourth competitive visit to play the Rossoneri in San Siro in all competitions going back the Sixties. Two of the previous three resulted in draws, the other defeat.

In fact Chelsea’s last Champions League win on Italian soil was the 4-0 thrashing of Lazio back in November 2003 and we have lost each of the past five such trips, including last season’s 1-0 at Juventus.

European centurions

Chelsea notched up a Pierre-Emerick Aubameyang’s close-range dispatch against AC Milan on Wednesday was the Blues’ 300th goal in all European competitions (including qualifiers). It helped Graham Potter to secure his first win and the club’s 100th in the Champions League since 1999.

EUROPEAN GOAL MILESTONES
100th Jimmy Floyd Hasselbaink (Zilina, Champions League, 26 August 2003).
200th Oscar (Nordsjaelland, Champions League, 5 December 2012)
300th Pierre-Emerick Aubameyang (AC Milan, Champions League, 5 October 2022)

The sighs of San Siro

AC Milan’s 3-1 Group E success against Dinamo Zagreb on matchday two was their first Champions League win at home since Virgil van Dijk’s Celtic side were beaten 2-0 in September 2013.

In the intervening nine years they qualified for Europe’s elite competition just once, in 2021/22, and six winless games there since were evenly split between draws (Ajax, Barcelona and Porto), and losses (Atletico, twice, and Liverpool last December).

What’s required to qualify?

Chelsea’s 3-0 defeat of AC Milan was potentially group-changing. Group E is the tightest of the eight, with two points separating all four members. The top two will progress to the knockout stage, third best drops into the Europa League.

In the event of any points tie the club with the better record in head-to-head results is placed above the other, so Milan would need to win by four clear goals to have supremacy should the two clubs’ final tallies be the same. Likewise, Chelsea could need to better the 0-1 defeat when Dinamo visit next month, or improve on our home draw with RB Salzburg when we take the Alpine air at the end of the month.

Champions League fixtures

Tuesday 11 October fixtures

• FC Copenhagen v Man City 5.45pm

• Maccabi Haifa v Juventus 5.45pm

• Celtic v RB Leipzig 5.45pm

• Dinamo Zagreb v RB Salzburg 8pm

• Dortmund v Sevilla 8pm

• AC Milan v Chelsea 8pm

• PSG v Benfica 8pm

• Shakhtar Donetsk v Real Madrid 8pm
  

Wednesday 12 October fixtures

• Atletico Madrid v Club Bruges 5.45pm

• Napoli v Ajax 5.45pm

• Barcelona v Inter Milan 8pm

• Bayer Leverkusen v Porto 8pm

• Plzen v Bayern Munich 5.45pm

• Rangers v Liverpool 8pm

• Sporting Lisbon v Marseille 5.45pm

• Tottenham v Eintracht Frankfurt 8pm