Serie A has long been regarded as one of the strongest football leagues in the world. Great Britain might be hailed as the country where football came from, but Italy is the one where it became more than a sport – an art!
And no two clubs are more representative of that change than Roma and Milan – two titans of Serie A, with a heated rivalry dating back even before Italy’s top league was founded, with rich historical context and significantly different views on how football should be played. Join us as we explain all the juicy details of their mutual history.
Historical Context: How and When Did the Rivalry Start?
Despite being founded at different times, Rossoneri (Red-and-Black, Milan’s historical nickname due to the uniform’s colors) and Giallorossi (Yellow-and-Red, Roma’s colors) predate Serie A as it is known today.
Milan was there earlier – in 189i, as the club was founded, the exact year the tournament started as a series of regional competitions. AS Roma, on the other hand, was born in 1927, after the unification of the three biggest Roman clubs at the time: Fortitudo, Alba-Audace, and Roman.
Italy’s biggest football league was established in its current form in 1929 and has proceeded as an annual round-robin tournament since. However, as a lesser-known fact, the first time Milan and Roma crossed paths occurred a bit earlier than that.
In a friendly match, the rivalry started on June 16, 1929, when Roma won an away game 1:0. Still, in their first official match later that year, during the Serie A bout, Milan was proclaimed the winner after winning 3:1.
Since then, the clubs have played an astonishing 201 times against each other, and the history of AC Milan was a bit more successful compared to their Roman counterparts.
- Milan has won 85 times out of 201.
- Roma turned out to be the winner a total of 53 times.
- And 63 times, a tie was proclaimed.
Ultimately, this rivalry represents much more than simply a game of two clubs and has deep roots in the history of both regions. Roma describes the capital, and while Italy was divided for most of its existence, the storied legacy of an eternal city lives strong in its community.
The club defends the honor of the historic, cultural center of the country, a town that unifies Italians as a symbol. Meanwhile, Milan is the financial centre of the country, the most fiscally and industrially successful part of the country, rivaling Rome’s history with its economic power (which is especially important for players!), which gives additional significance to each match between these teams.
So, despite not being a derby, which is a term reserved in Italian football for rivalries within the same city (such as Roma vs. Lazio in the Derby della Capitale and Milan vs. Inter in the Derby della Madonnina), the importance of this match should not be underestimated, especially concerning the fans, both the notoriously picky and demanding Milan Ultras and the highly prominent Roman football fans.
A Clash of Styles: What Can One Expect From Each Team?
That difference in budget and historical context has led to two styles that each team represents. Historically, AC Milan practiced catenaccio – a specific defence-oriented Italian football tactic that focuses on an unbreakable defence and successfully executing rapid counterattacks.
This later evolved into what’s known today as “total football,” concentrate on overwhelming ball possession and relying on a robust roster of star players, each of whom may lead the team to victory.
That star-studded team of Sacchi, Capello, and Ancelotti has made each AC Milan game an unmissable event and turned the rivalry with Roma into a highly one-sided affair – Milan rarely lost a game at home. He won all the finals where he met Roma.
Currently, the team is different – it still, as in its glory days, focuses on the attack but plays carefully and pragmatically. Despite the difficulties in the 2024-25 season, the team went through a renaissance starting with their 2022 Scudetto season, which turned them back into a favourite at different betting sites.
The club’s resurgence has not only attracted attention from football fans but also from bettors, with Mel Bet users and those on other sports betting websites increasingly choosing Milan as a team worthy of their wagers.
The odds and betting markets often reflect Milan’s improved form and the excitement surrounding their matches, making them a popular pick for both single-game and accumulator bets.
Roma, on the other hand, has always played football as if it was an improvisation. They preferred to attack en masse, which led to glorious victories and crushing defeats, which earned them a tremendous number of international fans.
They’ve changed a lot in recent years, starting with the appointment of José Mourinho as a manager. He restructured the team’s tactics, adopting a Catenaccio approach – not a whole tactic, but a style of careful and reactive football, primarily based on smart counterattacks.
The team continues to employ that clever style, currently under Claudio Ranieri’s management, and it has proven to be a successful strategy.
Roma vs Milan: Stats Throughout History
Both of these clubs have a long and storied legacy far beyond their direct confrontations. AC Milan history, in particular, dates back more than a hundred years into the past, and we can explore the most important stats and accolades both clubs have earned throughout their history to compare their successes.
- Scudetto: Milan has won Serie A 19 times, including three consecutive titles from 1991-1992 to 1993-1994, while Roma has won Serie A only three times, the last being in the magnificent 2000-2001 season.
- Coppa Italia: The only state where Roma leads the charge, with nine wins of the Italian Cup over 5 Milan’s five victories.
- International tournaments: an overwhelming Milan’s domination, with 7 Champions League victories, while Roma’s record got its first notch only recently: with Mourinho, they’ve won the inaugural UEFA Conference League trophy.
Key Figures of Milan and Roma Rivalry Across the Years
In almost a hundred years of historical rivalry and more than 200 matches played between AC Milan vs Roma, many figures can prove vital to understanding the competition and drama in each game between these clubs.
The rivalry of De Rossi and Gattuzo, Gunnar Nordahl, who scored for both clubs in their direct confrontations, or Pietro Paolo Virdis, who let Milan to many victories, however, the best the history of this rivalry uncovers themselves through two men – Francesco Totti and Paolo Maldini.
Totti has always been the heart and soul of Roma – more than just a captain, a symbol of the club. He played for the club for 25 seasons and has become a headliner in the confrontations with Milan, scoring 11 goals in all of their head-to-head games, more than anyone in history.
And if there was a man who could stop him, it was Paolo Maldini – his complete opposite. When Totti played with passion, Maldini was always calm. One was his club’s top scorer; the other was a rock who held Milan’s defense together for more than a few dozen years.
Both played against each other’s club more than 30 times, yet they stayed rivals, not enemies. Even recently, Totti praised Maldini, despite stating previously that Milan is the single team he liked scoring against the most.
Conclusion: What Waits for Us in The Future
Despite shared history and hundreds of matches against each other, Roma and Milan’s rivalry is far from over. Both teams are currently seeking to return to form and regain positions that will allow them to qualify for the Champions League in the Serie A tournament table.
Their next confrontation is scheduled for May 18, 2025. We’ll witness many more direct matches between these legendary teams in the future. Let’s hope another hundred years of their shared history will be as exciting as the first!
