Having advanced to the round of 16 with a nailbiting win at Udinese on Wednesday, Fiorentina head north again. This time, they’re heading north and west for a date with table-topping AC Milan. In 173 competitive fixtures dating back to 1931’s season-opening Serie A, the Viola have straggled to a W50 D48 L75 record against the Rossoneri, although that improves to W3 D3 L4 over their past 10 Serie A meetings. Indeed, Fiorentina steamrolled a hapless Milan side in this fixture last year to the tune of a 1-3 thumping that didn’t even come close to summing up the visitors’ dominance. That was maybe the last fun moment of Vincenzo Montella’s second spell in charge.

The referee for this one is 35 year old Rosario Abisso of Palermo. In 3 Serie A matches this year, he’s handed out 9 yellow cards and 1 penalty. He’s always been pretty slow with the cards, so don’t expect too many bookings unless there’s something egregious. In the 7 Fiorentina matches he’s directed, the Viola are udefeated: 6 wins and 1 draw. That said, he’s more than capable of mind-boggling blunder; he was the man in charge for that wild 3-3 draw against Inter Milan a couple years ago that saw him give Fiorentina a genuinely absurd equalizing penalty in the 96th minute. Last we saw him was in the season opening 1-0 win over Torino.

The match will be played on Sunday, 29 November 2020, at 2:00 PMGMT/9:00 AM EST at the Stadio San Siro in Milan. The forecast calls for one of those strangely cool but humid evenings you get in northern Italy, but there’s no chance of rain and the wind’s staying low despite the clouds, so it should be a lovely setting.

AC Milan

In a turbulent season full of unexpected twists and new beginnings, Milan have shot out to the top spot in Serie A, earning 20 points from their 8 matches. They boast the division’s 3rd-best attack (19 scored) and the 3rd-best defense (8 conceded), and even the Expected Goals table thinks they deserve their spot, which makes you think this isn’t just a fluke. They’re yet to lose in domestic play, although a 0-3 rout at home to Lille in the Europa League makes posed some questions. They will be coming off short rest from the return leg against les Dogues (a tough draw), so we could see a heavily rotated side.

Manager Stefano Pioli (who is a wonderful man and fully deserves his success) does have some injury issues to deal with up front. CF Zlatan Ibrahimović (thigh), LW Rafael Leão (hamstring), and RW Alexis Saelemaekers (ankle) have all been ruled out, so the Piolus will have to figure out who’s got the energy to do the work. Ibra in particular is a massive absence, as his 10 goals lead the club; the only other players in the side to have more than one in the league are Leão and Frank Kessié, who’s scored twice from the spot.

It’ll be interesting to see how Pioli changes his approach with Zlatan’s aerial dominance missing. Milan have averaged 20 crosses per game and are caught offside more than any other club, indicating their desire to get in behind and then center it. Especially without Ibrahimović, expect to see a more deliberate Rossoneri side try to pass through the Viola defense, which is likely to sit deep and deny space in behind for pace merchants like Samu Castillejo and Brahim Díaz. The hosts will likely dominate possession and probe for spaces in the box, and will also probably shoot from distance more than they usually do.

Fiorentina

While an extra-time win in Friuli to advance in the Coppa is nice, it’s worth remembering that Fiorentina are still mired in 15th place with 8 goals from 8 games and haven’t beaten a team not named Udinese in Serie A since opening day. That’s uh pretty bad, honestly, and there aren’t any quick fixes for what certainly looks like a broken team right now.

New manager Cesare Prandelli (taking on just his third match) will likely be without CM Giacomo Bonaventura (ankle) and LW Franck Ribery (thigh) from the start, which limits his options after his team played 120 minutes on Wednesday. Pol Lirola, Lorenzo Venuti, Antonio Barreca, Alfred Duncan, and Patrick Cutrone could all get starts, depending on how tuckered out the usual XI is and how Prandelli wants to set them out. A loose 4-2-3-1 with a bunch of midfielders milling around the center of the park seems to be his go-to right now, but he’s also shown a willingness to tinker, so it’s tough to predict his exact plans.

Given Milan’s aerial dominance (2nd-best in Serie A), this probably isn’t a great game to toss crosses into the box. Since we all know that Pioli’s style will rely on man-marking in the midfield, the best approach may be to look for long passes to the strikers’ feet from the back; Igor and Nikola Milenković in particular excel in this department. If Gaetano Castrovilli and Sofyan Amrabat can find a meter or two of space, they should have license to drive forward in possession, and the Moroccan’s passing range could also be a major weapon against a very compact Milan outfit. But with the hosts likely to dominate possession, it’ll definitely be a counterattacking game from the Viola with a lot of work in the channels.

Possible lineups

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How to watch

TV: RAI looks like your best bet, but check the full international television listings here.

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Ted’s Memorial Blind Guess Department

Normally, I’d mark this one down as a pretty obvious defeat for the good guys and move on. However, with Milan looking at another Europa League fixture against Celtic on Thursday, this is the kind of game they could overlook. If José Callejón is healthy, too, the Viola will get a boost from having an actual winger in the lineup at some point, which could offer a lot of width down the right and catch the opposition out. Combined with Fiorentina’s recent history of playing the Rossoneri pretty tough, I’ll call it a 2-2 draw, with Christian Kouamé and the much-maligned Dušan Vlahović canceling out Rebić (of course) and Simon Kjær fro a set piece. But realistically, the Viola are probably not even that significant of a speed bump for this in-form Milan group.

Forza Viola!