AC Milan vs Bologna

Seeking to end a prolonged drought for Coppa Italia success, AC Milan and Bologna will face off on Wednesday evening at Rome’s Stadio Olimpico for this year’s final.

Just last week, the two sides clashed in Serie A, with Milan rallying to secure a 3-1 victory at home, but they now meet again in the capital with a trophy on the line.

In an intriguing lead-up to the cup final, Milan hosted Bologna at San Siro for a Serie A match last Friday, where a comeback triumph narrowed the gap to two points behind their opponents in the league table.

Trailing after Riccardo Orsolini’s latest goal in a stellar individual campaign, the Rossoneri appeared headed for defeat until Santiago Gimenez came off the bench to change the game’s course, netting twice around Christian Pulisic’s 11th league strike of the season.

This result marked Milan’s first run of four consecutive wins across all competitions this season—and in over a year—signaling their intent to close a turbulent campaign on a high note. A new tactical approach, yielding five victories in six matches, has awakened the Lombardy powerhouse.

Despite kicking off Sergio Conceicao’s tenure with a Supercoppa Italiana win in January, setting the stage for several comebacks, Milan later stumbled in Europe and struggled in Serie A, where they’re poised to finish outside the top six.

However, they recently dominated rivals Inter Milan 4-1 over two legs to reach the Coppa Italia final, extending their unbeaten streak against their Nerazzurri foes to five matches this season.

Milan advanced to the semifinals in commanding fashion, entering the competition at the round of 16 due to European obligations. After a 6-1 thrashing of Sassuolo in December, they ousted Roma, with Tammy Abraham scoring twice against his parent club.

Amid speculation that Conceicao may not stay beyond this season, he could shift that narrative by triumphing in another cup competition, having noted that Milan last won two trophies in a season in 2008.

Following their Supercoppa victory over Inter, Milan now aim to improve a modest Coppa Italia record for a club of their prestige: their only win in nearly five decades came 22 years ago.

Moreover, victory in Rome offers their clearest path back to European competition. Fans in the red-and-black half of Italy’s second city will hope their team can reverse a poor domestic cup-final record, with just one win in their last six attempts.

While Milan are more celebrated for their European Cup and Champions League triumphs, they’ve claimed the Coppa Italia only five times—yet Bologna face an even heavier historical weight.

Whereas Milan last won the Coppa Italia in 2003, Bologna have lifted it just twice, with their most recent victory in 1974 against Palermo via penalties.

This season, Bologna progressed past Monza and Atalanta BC to reach the semifinals for the first time since 1999, before Vincenzo Italiano’s squad comfortably defeated Empoli 5-1 on aggregate over two legs.

Overwhelming an Empoli side that fielded a makeshift lineup of youth and reserve players prioritizing their relegation battle, Bologna secured a 3-0 win at Stadio Castellani, with Orsolini’s opener paving the way for Thijs Dallinga’s two goals.

They sealed the tie at home, earning a 15th Coppa Italia encounter with Milan, where the Rossoneri hold a historical edge with six wins to Bologna’s four.

Bologna snapped a 13-loss, four-draw streak against Milan in Serie A with a win at Stadio Dall’Ara in February, but last Friday’s defeat at San Siro dampened hopes of back-to-back Champions League qualifications.

Faltering at a critical juncture, the Rossoblu have gone winless in their last three matches since Orsolini’s late volley against Inter and a victory over Empoli. Sitting seventh with two rounds left, they now depend on others’ slip-ups.

A pivotal two weeks lies ahead: after facing Milan in Rome, Bologna will take on rivals Fiorentina in the Derby dell’Appennino, before hosting Genoa on the final day of a memorable campaign.