The 2019-20 Serie A season has been a rather inconsistent one for Fiorentina. It has seen a fair share of impressive results against the bigger sides, but it has also seen some disappointing games against the likes of Hellas Verona, Lecce and Cagliari.

But this tactical analysis looks at one of La Viola’s best games of the campaign. It came against Milan at San Siro and might live long in the memory of Fiorentina fans.

Played on the 29th of September 2019, the game saw Fiorentina come into it at the back of a three-game unbeaten run. Their previous outing against Sampdoria saw them snap their 18-game winless run under Vincenzo Montella and before that, they had held Atalanta to a 2-2 draw and Juventus to a goalless draw too.

As for Milan, their run-in had been the opposite. The 2-0 loss to Inter in the Derby della Madonnina was followed by a disappointing loss to Torino, who came back from a goal down to seal all three points.


Under Marco Giampaolo, the rossoneri were getting to grips with a possession-based approach to the game, while Montella’s new 3-5-2 shape had been reaping rewards. Giampaolo’s side set themselves out in a 4-3-3- slightly different to the 4-3-1-2 shape that the Italian had been trying to inculcate into the team since his appointment in the summer of 2019.

Montella’s newfound 3-5-2 became briefly known for La Viola fielding two false nines in the same system. And like it was against Sampdoria, Franck Ribery and Federico Chiesa started upfront. The emerging Gateno Castrovilli started in the advanced midfield role, with Erick Pulgar playing as the enforcer from deep and Milan Badelj playing as the anchorman.

The Diavolo had summer signing Rafael Leao start on the left flank, with the misfiring Krzysztof Piatek starting up front. Suso began the game on the left. Ismael Bennacer, who impressed in the few games that he played in, started at the base of the midfield three. Franck Kessie and Hakan Calhanoglu played slightly further in a trademark narrow Giampaolo midfield.

This tactical analysis looks at the ways through which Fiorentina got hold of the central areas of the game, their ability to cut off midfield passing lanes and Milan’s inability to progress the ball enough to create significant chances.

As we go on, we will realise that Montella got his tactics spot on for the game and this analysis shows just how he did it.

Fiorentina man-to-man pressing

The manner in which Fiorentina pressed in this game was crucial to how the result was. The basic idea of deploying two false nines in his system for Montella was to make sure that Chiesa and Ribery could drop into the areas around the Milan deeper midfielders. The aim of that was to disallow Milan from building from deep and keep circulating possession.

And the duo used their pressing abilities to excellent effect, leaving their pressing shadows to haunt Kessie and Bennacer whenever they came deeper to receive the ball.

As seen below- Ribery and Chiesa are hardly bothered about keeping a check on Alessio Romagnoli or Mateo Musacchio. They are clearly more into keeping tabs on Kessie and Bennacer and are making sure that Gigio Donnarumma doesn’t play them in from a short pass.

Castrovilli is right in the mix as well, staying pretty much in the middle of both the Italian and the Frenchman. With the middle passing lanes blocked, Donnarumma is forced to play the ball wide.

Some seconds later, the ball is played back to Donnarumma, with Castrovilli doing a job on Bennacer and the two forwards blocking a potential pass for the Milan central defenders. On the Milan right, Dalbert is stuck pretty close to Davide Calabria as well. This leaves Theo Hernandez as the only spare man and that is where Donnarumma passes long.

Only a few minutes on, Fiorentina showed another glimpse of their man-oriented pressing in midfield. Castrovilli is still keen on marking Bennacer, but the pressing from Pulgar and Badelj enters the fray here. Milan’s insistence of keep the ball on the ground helps them in blocking out Calhanoglu and Kessie.

Interestingly, both Chiesa and Ribery are a bit more into occupying open spaces when the ball comes slightly further forward.

This was a key aspect of the game throughout. Perhaps, the main idea from La Viola and Montella was to force Milan into playing it long to Piatek or Leao- as they possess more aerial ability than Suso on the right.

This makes it simple for them to stop Milan from picking up second-balls in advanced midfield. The rossoneri could only stand a chance of doing that if Piatek actually won the headers with his back to goal.

That is exactly what happens in this instance. Musacchio is forced to play long to the Pole, who is aerially dominated by Pezzella and as a result, Milan lost possession. Either way, Fiorentina manage to close down every possible option for Piatek, if he had ended up winning that aerial battle with the Argentine.

Because of the advanced positions around Bennacer and Kessie that Castrovilli took up, Fiorentina transitioned to a 3-4-1-2 on a regular basis. And in turn, this gave the young Italian more freedom to use his technical abilities and dancing feet.

Giampaolo’s Sampdoria had a knack for playing through the opposition midfield by being central on the pitch. Fiorentina fed on this aspect and their struggles to do that and Milan’s insistence on playing centrally played it into La Viola’s hands.

This does lead to the first goal. Bennacer is marshaled by Castrovilli, while Pulgar is doing a job on Calhagnolu. Ribery and Chiesa are blocking the space, making sure that Romagnoli doesn’t play a grounded ball to the full-backs.  Amidst this confusion, the Italian defender plays a hurried pass to Calhanoglu but the Turk plays a sloppy pass right into Ribery’s feet.

Ribery’s dazzling dribble into the final-third helps La Viola win a penalty that their usual taker Pulgar slotted away.

Fiorentina in transition/possession

Fiorentina’s pressing all across the pitch was massive in determining the result of the game and Milan helped them in that regard. But Montella’s men were direct and quick in their attacking transitions as well.

Ribery’s positioning was crucial, as he was the one to drop deeper between the lines to receive the ball and allow the two younger players in Chiesa and Castrovilli to make in-roads forward.

This allowed them to be fluid in the shape of their front three and helped them bypass Milan’s midfield without too much difficulty.

Chiesa’s positioning in this game was crucial, as he was handed a free-role. Instead of sticking to a single flank, the Italian was regularly switching sides off the ball. Fiorentina were in their 3-5-2 shape in possession that can often look like a 3-5-1-1 with advanced full-backs and Ribery deeper. Badelj played the anchor-man role, with Castrovilli and Pulgar slightly further forward.

Castrovilli though, had keep following Bennacer and this allowed him to alter the La Viola shape to an occasional 3-4-1-2. With the ball in a deeper position, their main aim was to go direct to the front two and potentially use over-laps from the wing-backs to overload the Milan defence.

The play from above developed in this manner too. Caceres played a long-ball out for Chiesa, who had Lirola moving into the space forward. This left Theo Hernandez in a 2v1 situation near him.

They constantly used Ribery’s ability to pick up the ball, turn and run by playing him in on a regular basis. As shown above, he had the license to drop deep and receive the ball and drive forward with his searing pace.

Milan off the ball/pressing and in possession

While Fiorentina’s pressing in the final third was really sucking the air out of Milan’s lungs, the rossoneri were trying with a press of their own too. Even though Giampaolo’s men weren’t as adept in that regard, they were still trying to make things happen. Unlike how they had to play out from the back, Fiorentina had zero hesitation for going long from the back (as pictured above).

In this passage of play, Milan are clearly trying to avoid Milenkovic from building play out from the back. The Serbian understands that and he plays a long-ball to Castrovilli instead of playing it down the right for a free Lirola.

Fiorentina’s approach on the ball in the first-half denied Milan too much hold when they pressed. Unlike the rossoneri, they didn’t play it into their hands and countered their pressing approach well enough.

In possession though, Milan looked to switch to Giampaolo’s usual 4-3-1-2 or 4-3-2-1. To do that, Rafael Leao drifted to central area and Suso moved into the right central channels to act as the playmaker. Because of this, Hernandez and Calabria could move forward into attacking areas.

This used to be a key feature of Giampaolo’s Samp teams, where the midfield would stay central and the front-three would get a lot of the ball. In the first-half of this game, Fiorentina tried their best to not allow the front-three into getting on the ball too much and that threw a spanner in the works for the Diavolo.

Milan did try playing long-balls to Piatek though. In this scenario late in the first-half, they did take that approach.

But once again, Pezzella being very close to Piatek made it next to impossible for them to win the first header and then take advantage of the second-ball. Suso and Leao are in the wide channels, but Milenkovic and Caceres clearly have given them no room to potentially pick the ball up.

On a general note, this is pretty much how the first-half panned out. Fiorentina’s gameplan worked perfectly and hardly allowed Milan any clear cut chances, restricting them to an XG of only 0.35. But Montella’s men had an impressive XG output of 1.44 in the first-half and that is a fair reflection of how their approach turned out to be very effective.


Fiorentina were right on the task in the second-half and from the get go, their dynamic frontline came into play once again.

And it was Chiesa’s determination to run into the channels constantly that caused Milan problems from the very first minute. With Lirola advanced, Chiesa dashes into space behind Hernandez- catching him out once again. Pulgar picks his run out with a simple through pass forward too.

Once Chiesa picks the ball up in space behind Hernandez, Fiorentina are in an advantageous position in the final-third. That is largely because of how Ribery and Castrovilli have sneaked behind Bennacer and the newly-introduced Rade Krunic. There is clearly a 3v3 situation that La Viola were really looking for throughout the first-half.

Not just that, but left wing-back Dalbert is also free down his flank and is pushing forward too.

The move doesn’t lead to a goal, as Chiesa’s issues about picking up the final ball came to the fore once again. But these were very promising signs for them with the game only set to heat up with time.

What is even more interesting is how Milan try to launch the ball forward at the end of this attack, but Pezzella marks Piatek out all over again to difuse another long-ball from the back.

Within ten minutes of the second-half starting, Musacchio was sent off for a high challenge on Ribery. And as soon as that happened, Giampaolo evidently asked his team to change to a 4-4-1 shape with Piatek the sole man upfront. To make up for the lack of a defender, Leo Duarte was brought on right away to play at centre-back.

Before Duarte came on though, the plan from Milan became clear. Leao positioned himself as a wide forward- like Mario Mandzukic often would at Juventus. And Donnarumma hoofed the ball upfront towards Piatek and Leao. This was a clear change in plan from the rossoneri.

It was misfiring Piatek himself who made way for summer signing Duarte, leaving Leao as the sole man upfront. By this time, the San Siro had grown silent and the rossoneri struggled to maintain any momentum. Fiorentina were still pressing in the same way, restricting supply from the back. Milan gave passes away and this piled the frustration on at the San Siro.

Fiorentina’s pressing remained quite the same. Castrovilli was still pro-active in that aspect and Chiesa was still making sure that the central defenders don’t play tehe ball sideways or backwards. He is creating the pressing shadows that will stop Romagnoli from passing back to Donnarumma. The only option for Romagnoli is to play a longer ball wide to Calabria or hoof it forward.

In an interesting passage of play some moments later, Donnarumma does opt to play it long to Calhanoglu. The former Bayer Leverkusen man does take the ball down well with his chest, but that is when Chiesa’s intense pressing comes into play once again.

Instead of seeking help from someone else to close Calhanoglu down, the Italian chases behind the Turk and presses him so much that he finds himself in Fiorentina’s defensive third.

The huge distance between the two players is clear above. But Chiesa still manages to cut the distance short and drive Calhanoglu into the opposite half. This is a fair reflection of how La Viola were just trained to press Milan in that way in this game.

It just shows the work-ethic Chiesa has and how Fiorentina were very well-drilled to do their job on the night. They worked very hard off the ball and even after Calhanoglu passes the ball back, Chiesa still nearly wins the ball from Donnarumma.

And it was La Viola’s man to man pressing all across the pitch that led to the goal, apart from Chiesa’s ability to run into the wide channels.

Milan try to build from the back again, but Milenkovic muscles Calhanoglu off the ball. He then spots Chiesa’s run and plays him in. Chiesa’s cross is deflected by Donnarumma but it is Casrovilli managed to put itinto the back of the net.


The fluidity in attack also plays a key role. With Ribery running down the left channel and Castrovilli centrally, Milan are in a 3v4 situation with Fiorentina having quick players running forward.

Chiesa’s ability to run into the wide channels was immense in Fiorentina’s third goal as well. The Italian was right behind Hernandez- the way he wanted to be all the game. Ribery was also picking up positions behind Calabria on the right, with Castrovilli attempting to pick them up from the central areas.

That clearly worked in the third goal, as the young midfielder found Chiesa perfectly and the Italian set Ribery up for a well-taken goal.

The goals in the second-half are a mirror into how Fiorentina dismissed the idea of playing it long. They did rely on that quite a bit in the first 45 by creating overloads in wide areas but the direct running of their two forwards brought about a change in their approach.


Milan’s goal came through Leao’s individual brilliance late in the game, but their approach in the second-half was a bit different from how it was in the first-half. Their attempts to go long were more desperate, as La Viola managed to force them into doing just that.

As the goals suggest, Montella’s men began relying on the wide channel exploitation of both Chiesa and Ribery as the game went on. In the first-half, they did rely on long-balls forward (as mentioned above). But their plan changed as the game progressed.

What is also interesting to note is that numbers-wise, Milan seem to have a better PPDA than Fiorentina, whose metric stood at as much 25.9 in the first-half. But it is also a reflection of how their approach to passing changed.

Since the rossoneri were more keen on playing out from the back in the first 45, Fiorentina’s PPDA numbers from that phase looks pretty high than the eye test would suggest. And Milan’s PPDA is much lower because Fiorentina weren’t bothered about playing out from the back in the Giampaolo manner.

With the passage of the game, they did begin to keep the ball on the ground more and perhaps, that is why they won the game in a pretty convincing manner. Ribery was applauded off by the San Siro in what was a brilliant performance from the summer signing.

Neither Montella or Giampaolo lasted long enough at their clubs. Giampaolo’s system couldn’t work out like many wanted and he maybe needed more time. As for Montella, his tactical flexibility didn’t shine through in many other matches and Fiorentina lost to lesser sides in the last few weeks of his tenure.

But this was one game that will live long enough in the memories of Fiorentina fans, irrespective of all that followed.