Dilemmas, droughts and the desire for revenge: The sub-plots to the Coppa Italia final

SempreMilan

·12 de maio de 2025

Dilemmas, droughts and the desire for revenge: The sub-plots to the Coppa Italia final

AC Milan will take on Bologna in the Coppa Italia final on Wednesday night, and for both teams it could be a season-defining game.

The fixture list presented us with an appetiser on Friday and Milan landed the first punch against Bologna in what is a double challenge over five days. The Rossoneri came from 1-0 down – as they so often have under Sergio Conceicao – and eventually emerged 3-1 winners.

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After a cagey first half that resembled a training session more than a Serie A six-pointer, the game burst into life after the break with Riccardo Orsolini opening the scoring. Santiago Gimenez came off the bench and scored twice, either side of Christian Pulisic putting Milan ahead.

Now, all attention turns to the capital and to the Olimpico, where Milan and Bologna will walk out alongside each other again but this time with silverware on the line. With that comes plenty of narrative.

A dish best served hot

The saying ‘revenge is a dish best served cold’ means that taking revenge is most satisfying when it’s done deliberately and after a period of time, rather than impulsively. However, Bologna are hoping that it is in fact piping hot and sweet.

Orsolini, who scored the opener at San Siro a few nights ago, certainly made it clear that he and his team-mates feel disappointment that Milan were able to deal their Champions League ambitions a major blow.

“We were ahead and we thought we could control it, Milan didn’t give the impression of wanting to attack, we gave them the spark that rekindled them and we got sliced through like butter. If we play like that in Rome we’ll get slapped. We’ve understood what we shouldn’t do,” he told Corriere della Sera.

On the other side, Theo Hernandez and Rafael Leao are returning to the scene of the crime in some ways. Back in September, when Paulo Fonseca was still the head coach, the cooling break saga ended up going viral during a 2-2 draw at the Olimpico.

During a water break whole team had approached the bench to listen to the coach’s words but Theo and Leao remained on the other side of the pitch. The two want revenge after what happened a few months ago, and they want to lift their third trophy since joining the club.

Photo by AC Milan

Droughts to end

It’s been seven years since the Rossoneri reached the final of the competition, and 22 years since they won it. On the last two occasions Milan were beaten by their rivals Juventus, and this time there was no possibility of playing the Bianconeri given they were knocked out by Empoli in the quarter-finals.

The last time that the Diavolo celebrated winning the domestic cup, Rome was again involved, or more specifically Roma. Back then the final took place over two legs, and after Milan won 4-1 in the first leg away from home they basically had the trophy in their pocket.

Bologna will face Milan in their first Coppa Italia final for 51 years, after a 2-1 second leg win over Empoli meant a 5-1 aggregate triumph in the semi-final. Giovanni Fabiana and Thijs Dallinga scored at the Stadio Renato dall’Ara, either side of Viktor Kovalenko’s equaliser.

When the Rossoblu won it in 1973-74 they had to go through Milan but in the group stages, taking four points from them to finish atop the group. They would eventually go on to beat Palermo on penalties at the Olimpico, after a 90th-minute spot kick had got them there.

Contrasting formations

The switch to a 3-4-3/3-4-2-1 formation seems to have changed Milan for the better. In a recent analysis we broke down just why it is giving some extra solidity, as shown by the three goals conceded in six games using three central defenders.

However, that doesn’t tell the full story. In fact, the last two wins were both comebacks against Genoa and Bologna, and they came via an in-game system change. Conceicao by his own admission went to a 4-2-3-1 in both games with the introductions of Joao Felix and Santiago Gimenez proving crucial.

The squad was certainly not built to play with three at the back, but as he admitted after Friday’s game ‘the players believe in what we are doing’. At most, Conceiçao will make some small tactical adjustments, especially as a result of the return to the starting line-up of Rafael Leao.

On the flip side, Bologna’s identity under Italiano is very well defined: they will play a 4-2-3-1 from minute one and throughout. They aim to play attractive football, pressing high and moving the ball quickly through the thirds. It’s how they’ve penned the Rossoneri in for large parts of the two meetings so far this campaign.

Quality on the wings

Speaking of formations, the new system is geared towards creativity out wide for Milan. Rafael Leao is a ‘wild card’ of sorts because he did not feature in Friday’s league meeting because of the fact that he had to serve a one game suspension.

It will be the first final he has played from minute one, having come off the bench in the Supercoppa Italiana. He ended up being decisive in Saudi Arabia, setting up Tammy Abraham for the winner, but now he wants to write a page in the club’s history with a goal of his own.

On the other side, Christian Pulisic is also looking to be decisive again after scoring the winner on Friday. If you exclude the real forwards (first or second strikers) the American is the first Milan player to score more than 10 goals in each of his first two Serie A seasons with the Rossoneri since the days of Luciano Chiarugi (1972-73 and 1973-74), with 12 goals last season and 11 in this.

One fact unites Pulisic and Leao: with 23 goals and 17 assists starting from last season, the former Chelsea man is the second player in Serie A to have scored more than 15 goals and provided at least as many assists. The other is Leao.

On Bologna’s side is Riccardo Orsolini. The right winger has 18 goal contributions across all competitions this season, with his 15 goals – the most recent being against the Rossoneri – making him the top scorer under Italiano.

The 28-year-old is also their captain, showing his rise to a leadership role, and he has been linked with a move to Milan in the summer transfer window, potentially as a replacement for Samuel Chukwueze. The Nigerian however did well off the bench a few nights ago, adding further overlap and intrigue.

Photos by Marco Luzzani/Getty Images and Alessandro Sabattini/Getty Images

Comebacks

Prior to the Serie A contest, Milan had earned 19 points from losing positions in Serie A in this season, whilst Bologna had gained 18 points. The Rossoneri and the Emiliani were the two teams with the most points picked up in this ranking in Serie this season.

After that win, the Diavolo have become the comeback kings in Italy with 22 points gained from losing position, 19 of which have been claimed with Conceicao in charge. This is as many points as Liverpool have gained from losing positions as well, while Man City are at 20.

The best in Europe’s top-five leagues are not Milan, though, but rather Diego Simeone’s Atletico Madrid who have clinched 23 points from losing positions. Still, the Rossoneri’s record is incredibly impressive, even if it would be better not to concede that first goal at all.

What Bologna have shown though is that they have plenty of talent on the bench that can come on and change games too, and that is why the starting XIs might not end up being decisive in the capital.

Manager paradox

Sergio Conceicao is quite simply put a cup specialist. As a player he won the Portuguese Cup and the Portuguese Super Cup with Porto, plus the Coppa Italia, Supercoppa Italiana, UEFA Cup Winners’ Cup and the UEFA Super Cup while he was a Lazio player.

As if the seven as a player weren’t enough, he won eight domestic cups (plus three Primeira Liga titles) while manager of Porto too. He won the Portuguese Cup in 2019-20, 2021-22 and 2022-23, showing that he has a knack for winning the premier domestic tournament.

Conceicao even has a trophy while at Milan and it came just a few days into his tenure, that being the Supercoppa Italiana of course. Vincenzo Italiano, by contrast, probably hates finals by now given he has always been the bridesmaid.

Italiano never won a cup while a player (only Serie B twice), while with Fiorentina he lost in the final of the Coppa Italia in 2022-23, the Conference League the same season and then also in the Conference League last season.

While history is heavily tilted in favour of Conceicao, what is even more bizarre is that the Portuguese could win a 13th trophy as a manager and a second in a few months with Milan but then step down, possibly to be replaced by the man he hopes to beat on Wednesday.