Italian Cup final: AC Milan eye another trophy as Bologna chase redemption.
On May 14, 2025, the Stadio Olimpico in Rome hosts a thrilling Coppa Italia final as AC Milan, led by cup specialist Sérgio Conceição, take on Bologna, a team seeking their first major trophy since 1974.
A Clash of Histories and Ambitions
The 2024-25 Coppa Italia final brings together AC Milan, a club with a glittering trophy cabinet, and Bologna, a side desperate to end a 51-year wait for major silverware. Milan, who last won the Coppa Italia in 2003, are chasing their sixth title in the competition, while Bologna’s last triumph came in 1974, marking their most recent major trophy. This final, a clash between a cup specialist and a serial runner-up, is a chance for both teams to etch their names in history and secure a Europa League spot for the 2025-26 season.
Milan’s Trophy-Laden Legacy
AC Milan, under the stewardship of Sérgio Conceição, are no strangers to success, though their last Coppa Italia victory was 22 years ago. The Rossoneri have reached the final 13 times but lost two in the intervening years. This season, Conceição, who took charge just five months ago, has already delivered the Supercoppa Italiana, his 12th trophy as a coach and ninth in cup competitions. With seven cup titles as a player for Porto and Lazio, Conceição’s knack for knockout success makes Milan favorites. However, sitting eighth in Serie A with only a slim chance of Champions League qualification, a Coppa Italia win is critical to salvaging a season marred by an early Champions League exit against Feyenoord.
Bologna’s Quest for Redemption
Bologna, led by Vincenzo Italiano, are the underdogs with a point to prove. The Rossoblu haven’t lifted a major trophy since their 1974 Coppa Italia win, and Italiano, who lost three finals as Fiorentina’s coach (two Europa Conference League finals in 2023 and 2024, and the 2023 Coppa Italia), is determined to shed his “bridesmaid” tag. Despite losing stars like Joshua Zirkzee and Riccardo Calafiori, Italiano’s high-pressing 4-2-3-1 system has Bologna dreaming of a historic upset. A victory would be their first major silverware in over half a century and only their third Coppa Italia title, cementing Italiano as one of only three Bologna coaches to achieve this feat.
Tactical Showdown in Rome
The final pits Conceição’s 3-4-2-1 formation against Italiano’s aggressive 4-2-3-1. Milan’s switch to a three-man defense has been a revelation, yielding five wins in six games, with 14 goals scored and just three conceded. Christian Pulisic (17 goals, 12 assists) and Rafael Leão, back from injury, lead a potent attack, while Tijjani Reijnders’ 15 goals add midfield dynamism. Bologna, however, rely on Dan Ndoye’s pace and Riccardo Orsolini’s 19 goal contributions to unsettle defenses. The recent 3-1 Serie A loss to Milan exposed Bologna’s vulnerabilities, with Orsolini admitting, “We gave them the spark that rekindled them and we got sliced through like butter.” Italiano’s side must adapt to avoid a repeat in Rome.
Lessons from a Recent Defeat
The final marks the second Milan-Bologna clash in a week, following Milan’s 3-1 league win at the San Siro. Santiago Giménez’s brace and Pulisic’s strike overturned Orsolini’s early goal, denting Bologna’s Champions League hopes. “We were ahead and thought we could control it,” Orsolini told Corriere della Sera. “If we play like that in Rome, we’ll get slapped. We’ve understood what we shouldn’t do.” Bologna’s man-to-man pressing and direct style will test Milan, but Conceição emphasized the importance of winning duels, saying, “At Milan, what counts is winning trophies, and Wednesday we have a great chance.”
The Road to the Final
Milan’s path included a 6-1 rout of Sassuolo, a 3-1 win over Roma, and a 4-1 aggregate victory over Inter Milan in the semi-finals, with Luka Jović starring. Bologna, meanwhile, crushed Monza 4-0, edged Atalanta 1-0, and dominated Empoli 5-1 on aggregate. The teams met eight times in the Coppa Italia’s group stages between 1968 and 1977, with Milan leading 4-2 in wins, but this single-legged final at a neutral venue levels the playing field. Extra time or penalties loom as possibilities in this high-stakes encounter.
Key Players to Watch
Milan’s attack hinges on Pulisic’s clinical finishing and Leão’s flair, with Reijnders and Youssouf Fofana anchoring midfield. Defender Strahinja Pavlović must neutralize Orsolini, who remains Bologna’s dangerman. For Bologna, Ndoye’s ability to exploit spaces and Thijs Dallinga’s three goals in the competition are critical. Goalkeeper Łukasz Skorupski’s heroics, like his double save in the recent league match, could keep Bologna competitive. As Italiano noted, his team’s enthusiasm and determination will be key to overcoming Milan’s experience.
High Stakes and Uncertain Futures
Winning the Coppa Italia secures a Europa League spot, a lifeline for both clubs given their mid-table Serie A positions. For Milan, a second trophy under Conceição could ease pressure on the Portuguese coach, whose job remains uncertain despite his cup pedigree. “It’s not the moment to talk about my future,” Conceição said. “At Milan, you don’t have time. What counts is winning.” For Bologna, a victory would be transformative, rewarding owner Joey Saputo’s faith and giving Italiano his first major trophy. The contrast between Conceição’s cup-winning expertise and Italiano’s history of near-misses adds intrigue to this showdown.
A Celebration of Italian Football
The Coppa Italia final is a spectacle, complete with a pre-match light show and the trophy presentation by legend Roberto Baggio. Bologna fans, including singer Cesare Cremonini and veteran Gianni Morandi, are rallying behind their team, while Milan supporters hope for a repeat of their Supercoppa triumph. With pride, redemption, and European qualification on the line, this final promises passion and intensity at the Stadio Olimpico. Whether it’s Milan’s trophy-hunting legacy or Bologna’s long-awaited redemption, May 14, 2025, will be a night to remember.
