EDIT: This has been a long time coming. A combination of lethargy and a lack of access to Football Manager meant this post has been marked as ‘pending’ for about… oh, only two years.

Having resigned as England manager following a disappointing World Cup (I honestly cannot convey just how disappointed I was), I had a bit of a hiatus. I had left England in July 2022, and did not not take up a new post until November, when I would begin my first overseas adventure.

In case it wasn’t obvious from the title of the chapter, I was heading to Italy – to Serie A, and to AC Milan.

At the time of taking over, Milan were seven-time European champions, making them the most successful Italian club in Europe. They had been doing okay in the league but not brilliantly – hence why there was an opening.

My very first match? Well, it ended up being a whopper – away, to fierce rivals Inter Milan (well, they share the San Siro, so technically not away, but you know what I mean). I could have done without being chucked into the lion’s den but I guess there’s no better way to get to grips with a new league than to dive right into one of its most passionate derbies, and the new manager effect was working very well, with an 8-2 win for me (yes, you read that correctly).

I’d embark on a reasonable sequence of results, but would be a little surprised to exit the Europa League at the quarter-final stage (against Celtic), and the league campaign was dented by five defeats that happened before I’d even joined – three more defeats would befall my Milan side, but not in the Coppa Italia, that I would go on to win (thus maintaining my record of a trophy won in every season I’d been at a club side). I also squeaked into 2nd place in Seri A, thus ensuring Champions League football for the following season.

So who were the architects of my cup-winning first season in Italy? Stephan El Shaarawy (who right now plays for Roma) was a strong performer on the right-wing for me, whilst Pablo Albini (a regen) was pulling the strings in the centre of my midfield. My two best performers though, were Willian (on the left-wing, with an average rating of 7.72), and striker Almando Calvo (who scored 59 goals in 53 appearances).

So the 2022/23 season had ended on a reasonably positive note.

2023/24

My first full season at the San Siro would begin quite strongly. I would win my first seven league games, scoring 21 goals and conceding none. A bit of a blip followed soon thereafter, with only one win in five games slowing my progress. A sequence of eight consecutive victories put my title campaign back on track, and I would only suffer four league defeats over the course of the season to close out the title very comfortably – finishing 23 points clear of Fiorentina. 105 goals scored and 33 conceded emphasised the lethal attack of my side, and their confidence in defence.

Whilst Seri A was a resounding success (powered by 48 league goals from Armando Calvo), my Champions League fortunes would rock me to the core. I got Milan out of the group stages easily enough (despite a 7-2 away defeat to French side Marseille), and dispatched Tottenham, Roma and Barcelona en-route to the final (Roma were also my opponents in the Coppa Italia final – they beat me 4-2).

For the Champions League final, my opposition would be my old club Liverpool. It was rather poetic to face off against them on the biggest stage, but the result was devastating. Liverpool inflicted a bruising 8-0 defeat upon me, completely outplaying my Milan side in every respect. The nature of the defeat left me shaken in my confidence, reeling from what had happened. In fact it rocked me to the point where I felt my interest in the game diminish. I would start the 2024/25 season still at AC Milan, but would see out only about half the campaign before deciding – both metaphorically and literally – that I was done with Football Manager for the moment.

Onward to Lower Leagues

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