Fresh off its first Serie A win of the season, Fiorentina returns to the Coppa Italia. Having brushed aside Benevento, the round of 32, the Viola earned a Tuscan derby against the vile Pisa (boo hiss). It’s the second derby running for the Torri; they dispatched Empoli on penalties in the previous round. The match will be played Tuesday, 15 Septemeber 2026, at 20:00 GMT/3:00 PM EST, at the Stadio Artemio Franchi in beautiful Firenze.
Three things to watch for
1. Is Pisa up for it?
Pisa was pretty bad in Serie A last year and fully deserved to finish
last. The Nerazzurri only won two games. They deserved twice that many, though, because they gave Fiorentina all it could handle in a pair of draws. The defining characteristic of both matches was that Pisa wanted it way more, putting the Viola under constant pressure both in and out of possession and winning every 50/50.
Pisa hasn’t exactly taken to Serie B either, winning twice and losing twice so far, including a 1-4 walloping at home by Virtus Entella on Friday. That embarrassment, combined with the savor of getting on over on the club’s biggest rivals, could spur Paolo Bianco’s boys to unexpected heights. On paper, this one doesn’t look even close to even. With the added motivation of winning this Derby di Toscana, the difference in payroll and talent won’t mean nearly as much as the cliched Who Wants It More.
2. How much Vanoli rotates
It’s very early in the season so Paolo Vanoli doesn’t have to worry too much about his players’ legs getting overworked. Nevertheless, he may use this as an opportunity to get a better look at some of his backups as he evaluates the squad. He’s also got the added benefit of some goodwill from the fans after finally getting this Viola project off the ground with a win. Especially with all the late additions to the squad in the final couple days of the transfer window, he could see this as a perfect opportunity to test out Pedro Gonçalves and Wilfried Gnonto.
On the other hand, the mister might prioritize continuity over freshness. As he tries to inculcate his tactical and psychological principles into the team, he could follow the trail he blazed last year: minimal rotation to ensure that everyone understands their roles. Fiorentina’s about two months behind everyone else and this game gives the starters a free 90 minutes to catch up. I think we’ll see a couple changes but I doubt Vanoli’s going to do more than rotate a winger, a defender, and a midfielder.
3. Bozo moments at the back
I’m a huge loser and take notes while I watch games. One of the more frequent phrases I use when describing Fiorentina’s defenders is “bozo moment.” This has nothing to do with technical ability and everything to do with the mental side of the game. A bozo moment doesn’t happen when someone makes the wrong decision. It happens when someone decides to ignore multiple simpler options in favor of doing something much more difficult. Trying to dribble at the back when a teammate is right there for a pass? Trying to bring down a high ball instead of just heading it away? Looking for a cute infield pass when the goalkeeper or the down-line option are available? Ignoring a runner to go for the Hollywood tackle? Bozo moments.
The modern game, predicated on pressing and solidity, is designed to prey on the bozos in a way no previous era has. A defender used to be able to make a mistake but redeem themself with some personality (e.g. Lucas Martínez Quarta). Now, every system puts defenders in the crucible to see if they’ll crumble. Right now, the only solution anyone’s found is to have defenders who are physically and technically excellent. That’s a rare combination and the market (insomuch as Adam Smith’s entire ideology exists) guards it jealously. Those guys are scarce and expensive. A club like Fiorentina can rarely afford one, much less two; the last one in Florence was the perennially underrated Nikola Milenković.
Unfortunately, his peers and successors have all had that Bozo Gene. In Radu Drǎgușin and Luca Ranieri, it’s slightly less bozo than it could be; their faults are generally switching off. In Ranieri’s case, he gives opponents too much space to make up for his lack of athleticism. Drǎgușin, on the other hand, struggles to turn his head quickly enough to map the pitch. Marin Pongračić‘s bozo moments are a mix of insane passes and bizarre decisions to dribble forward. Viery, despite his age and (lack of) experience, has been the least bozo defender on the roster so far. Especially because Pisa will press high, the defensive solidity is more predicated on “don’t do something dumb” than it usually is. And that should make you, a Fiorentina fan, very nervous.
Possible lineups
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Ted’s Memorial Blind Guess Department
The odds tilt very heavily towards the hosts for all the reasons you’d expect: home team, Serie A vs Serie B, most recent result (Fiorentina won 2-4, Pisa lost 1-4), payroll/talent advantage, et cetera. Now that Vanoli’s at the helm, I can’t really argue any of those points. My only caveat is that derbies are always wacky and unpredictable. Would anyone be shocked if the visitors dug deep, chased a complacent Viola side all over the park, and stole a cheap goal somehow? Disappointed, sure, but shocked?
Even so, I believe in Vanoli to keep his guys geed up for this one. We’re still in the honeymoon phase, with the players wanting to impress the coach to earn their places in the hierarchy, and that should prevent the guard from lowering too much. I’ll call it a 2-1 for Fiorentina with goals from Arthur Atta and Pedro Gonçalves for the good guys and Matteo Tramoni pulling one back late for Pisa. It’ll still be a sweaty, unpleasant affair with the Nerazzurri pressing like maniacs before snapping back into their deep block. Were I a gambler (I’m not because even my dumb ass is too smart for that), I’d take the over on cards and, given the likelihood of bozo moments, I’d take both teams to score.
Forza Viola!
