Firstly, Chelsea and Milan – who knew so many players, several of whom can be considered football royalty, represented both teams? The list of forwards alone would leave the manager of this team, another man who sat in the dugout for the Blues and Rossoneri, with quite the selection dilemma.

Fortunately for us, this form of fantasy football is inconsequential, leaving us free to plonk some absolute legends on the bench.

• Where are the Class of '99 now?

• Chelsea vs AC Milan: Pre-Match Briefing

• Giroud on his return to SW6

One rule we have set, though, is that it must be limited to former players. That means the current batch of Pierre-Emerick Aubameyang, Thiago Silva, Olivier Giroud, Fikayo Tomori and Tiemoue Bakayoko are all ruled out for selection.

Let’s start with the goalkeeper, which is perhaps the easiest decision of them all. Asmir Begovic made a couple of appearances for AC Milan during a loan spell there in 2020, a few years after he won a Premier League title as back-up to Thibaut Courtois, while Marco Amelia also had a brief spell at the Bridge at the time, a few years after his spell with Milan.

But there’s only one man to don the gloves for this combined team: Carlo Cudicini. He may have been limited to only three matches for the Rossoneri – plus a spot on the bench for the first-ever Champions League final – but his father, Fabio, was a legend there and Carlo went on to become a Blues hero after joining us in 1999. At one time he was up there with the very best in the Premier League.

Our defensive options are also slightly limited, although that’s down to numbers – we’re going with a back three – rather than quality as we’ve got a couple of Champions League winners in here. Thiago Silva, however, would have been straight on the team sheet had he been available for selection.

Let’s start with a Brazilian centre-half who Blues fans might be left scratching their heads over, wondering just when he played for AC Milan. Alex, of course, was famous here for his blockbuster free-kicks and playing his part in our Double-winning campaign of 2009/10. He went on to finish his career at San Siro, scoring in a Milan derby during his two years in Serie A between 2014-16.

Marcel Desailly is the obvious choice to be the ‘rock’ at the heart of our defence, although he was often in midfield for Milan. He won a Champions League final for Marseille against AC, then joined them that summer and went on to score in the following year’s final against Barcelona. The World Cup winner spent six years as a Blue, when it could be argued he was one of the first truly world-class players to join the club.

The back three is completed by Christian Panucci, who was regarded as one of Europe’s top full-backs during his time with Milan and then Real Madrid, winning the Champions League with both. Gianluca Vialli signed him on loan for Chelsea in the summer of 2000 and was soon replaced by Claudio Ranieri, who clearly didn’t fancy him, and he barely featured for the Blues.

One man not troubling this team selection is Winston Bogarde, who played a combined 12 league games for the two clubs – and, you’ll be stunned to hear, the majority of those were for Chelsea!

That’s not so much of a problem for us when it comes to Brian Laudrup, who might not have featured often during short stints with the two clubs, but his ability to get chalk on his boots as a genuine wideman brings balance to our team. Some Chelsea fans may find this unforgivable considering he left us so soon after signing from Rangers in 1998, when he was thought by many to be the missing piece of the puzzle.

If our central midfield partnership doesn’t get you purring, it’s time to re-evaluate how you look at the beautiful game. First, we’ve got Ray Wilkins, one of Chelsea’s greatest midfielders. Butch came through the ranks to become our youngest permanent skipper and he could do the lot as a midfielder, which is often forgotten by those who only saw him in his later years. He later spent three years with AC Milan in the Eighties, where he was highly thought of – and that made him the obvious choice for punditry duties when Channel Four got the rights to show Italian football in the UK!

Alongside him is Ruud Gullit, the delightful dreadlocked Dutchman who was signed to replace Wilkins at San Siro in 1987, although he would often play as an attacker there. He joined them for a world-record fee, won the Ballon d’Or and helped them to two European Cups, scoring twice in the first final. So, you can imagine the excitement felt at Stamford Bridge when we somehow convinced Gullit to join us in 1995. He lit up an otherwise middling team and then went on to become manager, leading us to FA Cup glory in 1997 after 26 years without a major trophy.

Completing the midfield quartet, and making full use of his versatility, is Michael Essien. The Ghanaian is one of six players to leave Chelsea for AC Milan on his permanent basis, and though the Rossoneri only caught glimpses of his talent, we saw Essien at his peak in west London. He’d play anywhere, run all day and, to top the list of fan-favourite requirements, bang in the odd wonder goal.

So, there’s no shame for either Sam Dalla Bona – great for Chelsea under Ranieri, failed to live up to his potential with Milan – and Marco van Ginkel – hit by injury – failing to make it into this midfield.

That just leaves us with the three forward positions. Let’s start by going with those who haven’t made the list: Fabio Borini, Hernan Crespo – a Premier League title winner and scorer of two goals for AC Milan in a Champions League final – Gonzalo Higuain, Pato and Fernando Torres.

The first forward to make the cut is someone who, prior to Desailly, could arguably be considered the only player at their world-class peak to play for Chelsea. That man is Jimmy Greaves, who came through our youth system scoring goals and carried on sticking the ball in the back of the net at a rate that was up there with the very best. Those who saw Greavesy in his pomp liken him to Lionel Messi, so it’s a shame for AC Milan that they only briefly saw his talents in red and black.

Their fans would probably say likewise about Chelsea when it comes to our other two choices, both of whom were world stars with the Rossoneri but only briefly shone in blue. George Weah came to us on loan in January 2000 and promptly scored on his debut against Spurs, but there wasn’t an awful lot else to shout about during his short time here. With Milan, he was the first African to win the World Player of the Year award and Ballon d’Or, and he became something of a legend over here to Football Italia viewers after dribbling from his own half to score a famous goal against Verona.

Finishing our line-up is another Ballon d’Or winner, Andriy Shevchenko. The Ukrainian is immortalised in Milan after scoring the winning penalty in the 2003 Champions League final win over Juventus during a spell when he was widely regard as the best striker on the planet, prompting the Blues to sign him for a club-record fee in 2006. Although we rarely saw the best of him – an FA Cup stunner against Spurs aside – Chelsea fans had a lot of love for the effort Sheva always put in.

If you need us to tell you who’s managing this team, you’ve obviously not been following European football closely enough over the past couple of decades. It’s a two-time Champions League winner with AC Milan – and he lifted the trophy while a player at San Siro – and the only manager to win the Premier League and FA Cup ‘Double’ while at Chelsea. Over to you, Carlo Ancelotti.