While La Viola are bidding to progress from the last 16 for the third successive season, I Gialloblu are seeking to avoid crashing out at this stage for the fourth time in the last five years.
Following a run of just four wins in 10 matches across all competitions between the end of September and early November, Fiorentina have since come out on top in four of their last five games, including last weekend's 3-0 success over Salernitana in Serie A.
Two goals inside the opening 17 minutes from Lucas Beltran and Riccardo Sottil put La Viola in control on home soil, before Giacomo Bonaventura's second-half strike wrapped up the points for Vincenzo Italiano's side.
Fiorentina currently sit sixth in Serie A and just one point behind fourth-placed Roma, who they will face in their next top-flight fixture on Sunday, but they must first turn their attention to the Coppa Italia as they endeavour to avoid a cup upset against lower-league opposition.
La Viola, who beat Parma 2-1 over two legs in the 2000-01 Coppa Italia final, were unable to end their 22-year trophy drought in last season's showpiece event, as they lost 2-1 to eventual winners Inter Milan despite taking an early lead through Nicolas Gonzalez.
They now enter the last-16 stage determined to go one better this time around, but success over Parma on Wednesday is not a given as they have only won one of their last six meetings with I Gialloblu.
After falling short in the Serie B promotion playoffs last season, Parma have since made a strong start in the second tier this term as they have won 10 of their opening 15 games to climb to the top of the table, sitting level on points with Venezia.
I Gialloblu suffered a brief wobble in form when they dropped points against Lecce and Modena at the end of last month, but they returned to winning ways in dramatic fashion last weekend as they beat Spezia 1-0 away from home courtesy of a 94th-minute own goal from Joao Moutinho.
Fabio Pecchia's men have now won seven of their last nine away matches in all competitions this season, although Saturday's success over Spezia was the first time that they failed to score at least two goals on the road.
Two of Parma's seven away victories have taken place in the Coppa Italia, with a comfortable 3-0 win at Bari in the first round followed by a 4-2 triumph over Lecce in the second round last month – a game in which I Gialloblu scored two stoppage-time goals to progress to the last 16.
However, Parma have failed to progress beyond the last-16 stage of the Coppa Italia since the 2013-14 campaign when they reached the quarter-finals, and they have failed to win any of their previous four encounters with Wednesday's opponents Fiorentina, albeit drawing three of those in Serie A.
Fiorentina will be without full-back Dodo and teenage goalkeeper Tommaso Martinelli due to respective knee and thigh injuries, while Gaetano Castrovilli is still recovering from a long-term knee problem and will not be involved on Wednesday.
Italiano may consider making a few changes to freshen up his side, with Oliver Christensen hoping for a rare start in goal ahead of Pietro Terracciano, while Fabiano Parisi could replace captain Cristiano Biraghi at left-back.
Nicolas Gonzalez, M'Bala Nzola, Josip Brekalo, Rolando Mandragora, Lucas Martinez Quarta and Yerry Mina all began as substitutes last weekend and will be looking to force their way into the starting lineup on Wednesday.
As for Parma, Lautaro Valenti is closing in on a return from a long-term knee injury, but Wednesday's game will likely come too soon for the defender, while Roberto Inglese is doubtful with an unspecified issue.
Adrian Benedyczak, Parma's joint-top scorer this season along with Dennis Man (eight goals), missed last weekend's win at Spezia due to a fever, but the Polish forward could return in time to face Fiorentina.
Fiorentina possible starting lineup:
Christensen; Kayode, Ranieri, Martinez, Parisi; Duncan, Mandragora; Gonzalez, Bonaventura, Brekalo; Nzola
Parma possible starting lineup:
Corvi; Coulibaly, Balogh, Circati, Ansaldi; Sohm, Estevez; Man, Benedyczak, Mihaila; Bonny
We say: Fiorentina 3-1 Parma
Fiorentina cannot take Parma lightly considering their strong away form and solid start made in Serie B this season. However, the hosts will be regarded as favourites for Wednesday's cup tie and should have enough quality at their disposal to progress to the quarter-finals.
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