Prediction: AC Milan vs AS Roma

AC Milan and Roma face off in the Coppa Italia quarterfinals on Wednesday, both seeking to move past their recent Serie A struggles and claim a spot in the semifinals.

Following dramatic finishes in their high-profile league matches last weekend, the two sides will meet at San Siro for this midweek cup showdown.

AC Milan

A month after their five-goal thriller in Riyadh, Milan and Inter met for a more traditional Derby della Madonnina on Sunday, with the Rossoneri seeking a third win over their city rivals this season.

Sergio Conceicao’s side came agonizingly close, holding a lead from Tijjani Reijnders deep into stoppage time until Stefan de Vrij’s last-minute equalizer denied them victory.

As a result, Milan remain far behind in Serie A, trailing second-placed Inter by 16 points. They currently sit eighth, battling for European qualification amid an inconsistent campaign.

Despite securing the Supercoppa Italiana last month, Milan aim to improve their modest Coppa Italia record, having last won the tournament nearly 22 years ago. Beaten by Atalanta in last season’s quarterfinals, the Rossoneri entered this year’s competition at the last-16 stage due to their Champions League commitments.

A December 6-1 rout of Sassuolo, featuring a Samuel Chukwueze brace, earned them a place in the quarter-finals. After Juventus and Inter, Milan (24) and Roma (22) have made the most semifinal appearances. Notably, Milan triumphed 2-1 in both legs of their most recent semifinal clash with Roma back in 2004.

Team News

Following a hectic week of transfers, Milan have signed Mexican striker Santiago Gimenez, while Alvaro Morata has moved to Galatasaray on an initial loan deal. Former captain Davide Calabria has also departed for Bologna.

Sergio Conceicao can now call on Youssouf Fofana, who returns from suspension, but Ruben Loftus-Cheek, Emerson Royal, and Alessandro Florenzi remain sidelined due to injuries.

With a league trip to Empoli on Saturday and a Champions League playoff against Feyenoord on the horizon, rotation is expected. However, Tammy Abraham is likely to retain his place up front.

AS Roma

Roma triumphed in their last Coppa Italia encounter with Milan, held 18 years ago, though they have not advanced beyond the quarterfinals since 2017.

In their most recent league meeting at the end of last year, the Giallorossi held Milan to a 1-1 draw at San Siro, with Tijjani Reijnders opening the scoring before Paulo Dybala’s equalizer.

Interim coach Claudio Ranieri, who returned to manage his boyhood club amid turmoil, has overseen a resurgence. Roma have climbed to ninth in Serie A and secured Europa League progress by defeating Eintracht Frankfurt.

Their resilience was tested last Sunday when league leaders Napoli visited Stadio Olimpico for the Derby del Sole. Former Roma full-back Leonardo Spinazzola gave Napoli the lead, but Angelino’s late strike salvaged a draw for the hosts.

Ranieri’s side are now unbeaten in seven league games after losing seven of the previous nine, though they have only secured one win on the road this season.

Team News

Roma have resolved fitness concerns regarding Manu Kone and former Milan player Stephan El Shaarawy, both of whom picked up knocks against Napoli.

As a result, suspended centre-back Gianluca Mancini is the only confirmed absentee for the midweek clash at San Siro, with Mats Hummels expected to return after being rested on Sunday.

Claudio Ranieri’s favored attacking duo, Artem Dovbyk and Paulo Dybala, were also benched for the Derby del Sole but are set to start. Dybala, who has netted 10 goals against Milan throughout his career, has only scored once against them in the Coppa Italia.

Conclusion

Claudio Ranieri has triumphed in six of his eight Coppa Italia ties during various spells as Roma coach, though securing a rare away win with this Giallorossi squad might be a tall order.

Despite Milan’s inconsistency, they demonstrated their potential in the Supercoppa and have become more resilient under new management, making them a formidable challenge at San Siro.

Verdict: Home win

Best odds: 1/1

Bookmaker: ZetBet