After surviving a huge scare in the playoffs, two-time finalists Fiorentina will continue their latest Conference League campaign on Thursday evening, when Rakow Czestochowa pay a visit to Stadio Franchi.
Having squeezed past Jagiellonia Bialystok last month, the Viola must now host another Polish side in the first leg of their last-16 tie, with a quarter-final against either Crystal Palace or AEK Larnaca at stake.
Match preview
With one foot apparently in the next round, Fiorentina welcomed Ekstraklasa leaders Jagiellonia to Florence having built a three-goal lead from the first leg in Poland.
However, Jaga were back on level terms by the 50th minute, and only two extra-time goals spared the Italian side's blushes as they ultimately won 5-4 on aggregate.
Conference League runners-up twice in the past three years - and the only club to score 100 goals in UEFA's third-tier competition - the Viola have struggled through this season's continental campaign.
Fiorentina's 15th-place finish in the league phase saw them slip into the playoffs, where they almost suffered an embarrassing exit in front of their own fans.
Paolo Vanoli's side have also been enduring a tough time on the domestic front, and they still face a scrap for Serie A survival.
Following a recent 3-0 defeat to Udinese and Sunday's home draw with Parma, they sit just one point clear of the drop zone - largely thanks to the dismal form of 18th-placed Cremonese.
Before resuming their relegation fight with a crucial clash against Cremo next Monday, Fiorentina will face their 12th knockout tie in the Conference League, after progressing from 10 of the previous 11 - the exception being last year's semi-final defeat to Real Betis.
Though the Tuscan club have also scored at least twice in each of their last six European knockout games at Stadio Franchi, they must now host one of the Conference League's most miserly defences.
Conceding just two goals across six outings so far, Rakow Czestochowa boast the second-best defensive record in this season's tournament, and that helped them cruise into the round of 16.
Unbeaten through the league phase, with four wins and two draws, they finished second to secure direct progress without needing a playoff.
Rakow are enjoying the most successful period in their history, having followed back-to-back domestic cup triumphs in 2021 and 2022 with their first league title one year later.
Runners-up in Poland's top flight last term, they then came through three qualifying rounds just to reach the Conference League proper, and they have certainly maintained that momentum.
By contrast with Fiorentina's woes, Lukasz Tomczyk's side are flying high in the Ekstraklasa; Sunday's 2-0 win over Pogon Szczecin left them fourth in the table, just four points adrift of top spot.
So, they are well set for a springtime trip to Tuscany, where they will meet Italian opposition for just the second time ever: Rakow lost twice to eventual winners Atalanta in the 2023-24 Europa League group stage.
Fiorentina Conference League form:
L L W L W L
Fiorentina form (all competitions):
W W W L L D
Rakow Czestochowa Conference League form:
W D D W W W
Rakow Czestochowa form (all competitions):
D D W L W W
Team News
Vanoli is set to rotate his squad, as he generally makes sweeping changes for European fixtures and Fiorentina face a vital league game next Monday.
Star striker Moise Kean missed out at the weekend with a shin problem, so Roberto Piccoli may be asked to continue up front, while Luca Lezzerini and Manor Solomon are still injured.
Fabiano Parisi can return from a one-match domestic ban, but Croatian centre-back Marin Pongracic will be suspended for this week's first leg.
Set to start in midfield, Rolando Mandragora has made the most appearances (45) and scored the most goals (nine) in the Viola's Conference League history.
Meanwhile, Rakow's top scorer in the competition is Lamine Diaby-Fadiga, who has found the net six times in 11 appearances - including qualifiers.
The French forward should support lone striker Jonatan Braut Brunes, whose opening strike on Sunday took his tally to 12 Ekstraklasa goals for the season.
Aston Villa loanee Oliwier Zych will start in goal, while ACL victim Vladyslav Kocherhin is the visitors' only confirmed absentee.
Fiorentina possible starting lineup:
De Gea; Fortini, Comuzzo, Ranieri, Parisi; Brescianini, Mandragora, Fabbian; Harrison, Piccoli, Fazzini
Rakow Czestochowa possible starting lineup:
Zych; Tudor, Racovitan, Svarnas; Ameyaw, Repka, Struski, Carlos; Diaby-Fadiga, Makuch; Brunes
We say: Fiorentina 1-2 Rakow Czestochowa
In Serie A, Fiorentina have only claimed 14 points from a possible 42 on home soil this season, and they remain very vulnerable at the back.
Also with one eye on Monday's relegation six-pointer, the Viola may lose to Polish visitors again: Rakow have already proven their capability, both in qualifying and an impressive stroll through the league phase.
For data analysis of the most likely results, scorelines and more for this match please click here.