Meeting in the semi-finals of a new-look Supercoppa Italiana, Serie A rivals Napoli and Fiorentina convene at Riyadh's Al-Awwal Stadium on Thursday.
For the first time, four teams will take part, and the Scudetto holders take on last season's Coppa Italia runners-up in the tournament opener.
Match preview
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While Inter Milan have won the last two editions of the Supercoppa and are now aiming for a hat-trick, Napoli have lifted the trophy traditionally decided between Italy's league champions and cup winners just twice in their whole history - the last success coming 10 years ago.
The Partenopei earned their place in this term's expanded format by ending a three-decade-long Scudetto drought last season, but their title defence was quickly derailed, and they now arrive in Saudi Arabia trailing far behind Serie A's top two, Inter and Juventus.
Led by a third coach in less than a year, Napoli began 2024 on a down note by losing for the fourth time in six league games - suffering a 3-0 defeat to mid-table Torino - and even after last week's late win against regional rivals Salernitana they sit eighth in the standings.
It took a stoppage-time strike from Amir Rrahmani to beat Serie A's bottom club 2-1 at Stadio Maradona, where they have particularly struggled this season - no doubt weighed down by the expectation of their fans - and Walter Mazzarri's men were certainly not convincing in victory.
Nonetheless, Napoli are just two points behind Lazio and Atalanta BC, and five shy of fourth-placed Fiorentina, so all is not lost in terms of salvaging Champions League qualification from a testing campaign - and they are also involved in the knockout phase of this term's competition.
Picking up some more silverware would surely boost morale at the Campanian club ahead of a big league clash with Lazio, who they could potentially meet in the Supercoppa final on Monday.
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First, though, the Italian champions must eliminate a Fiorentina side that left Naples with all three points in October, when the Tuscans ran out 3-1 winners thanks to goals from Josip Brekalo, Giacomo Bonaventura and Nico Gonzalez.
The Viola followed that success with three defeats from four games, but they have been on an upward trajectory ever since and now occupy a top-four spot in Serie A.
Despite taking only one point from their first two top-flight fixtures of 2024, Vincenzo Italiano's side remain on course for more European football next season, in addition to booking a place in the Europa Conference League's latter stages and a Coppa Italia semi-final against Atalanta.
Fiorentina's recent cup win over Bologna was sandwiched by a disappointing defeat in Sassuolo and last weekend's eventful 2-2 home draw with Udinese, which saw them escape with a point due to M'Bala Nzola staying cool from the penalty spot late on.
While Italiano has made a significant impact since arriving in Florence, losing in both the Coppa and Conference League finals last term will have left a bitter taste - particularly as it is now more than 22 years since the Viola last lifted a trophy.
Claiming the club's first Suppercoppa since 1996 - when Gabriel Batistuta's brace beat Milan - would partly make up for such disappointment, but Napoli now stand in their way of making another final.
Team News
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Napoli travelled to Saudi Arabia without star striker Victor Osimhen and midfield regular Frank Anguissa, both of whom are away at the Africa Cup of Nations - and they are also missing their first-choice goalkeeper.
Alex Meret (hamstring) again joins Natan (shoulder) and Mathias Olivera (knee) on the sidelines due to injury, so Pierluigi Gollini deputises as the Partenopei's last line of defence.
After sitting out Saturday's win over Salernitana, Piotr Zielinski could be back at Walter Mazzarri's disposal on Thursday evening; fellow midfielders Jens Cajuste and Diego Demme should also overcome knocks.
Meanwhile, Fiorentina can include recent signing Marco Faraoni, who set up Lucas Beltran's goal on his debut, and another right-sided player, Dodo, has resumed training following a long-term absence with an ACL injury - young Michael Kayode is still set to start, though.
Nico Gonzalez has resumed training, but Gaetano Castrovilli remains unavailable and Christian Kouame is representing hosts Ivory Coast at the AFCON.
Up front, Vincenzo Italiano will choose between Beltran and M'Bala Nzola, after both strikers scored on Sunday - the former is favourite to start, having netted half of the Viola's last eight league goals.
Napoli possible starting lineup:
Gollini; Di Lorenzo, Rrahmani, Jesus, Rui; Cajuste, Lobotka, Zielinski; Politano, Raspadori, Kvaratskhelia
Fiorentina possible starting lineup:
Terracciano; Kayode, Milenkovic, Martinez Quarta, Biraghi; Duncan, Arthur; Sottil, Bonaventura, Ikone; Beltran
We say: Napoli 1-2 Fiorentina (after extra time)
It may take more than 90 minutes to separate two well-matched sides, with neither having started the year sharply. Although Fiorentina do not tend to travel too well, their recent pedigree in knockout competition is notable, while Napoli are missing key players and clearly lack last year's cohesion.
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