The only city in European football to be the home of two Champions League winning clubs, the Milan divide is among the most intriguing on the continent.
Inter and AC Milan are both regarded as giants of world football, with their latest meeting a mouthwatering occasion as the two teams go head-to-head in the Champions League semi-finals.
It promises to be a fascinating showdown between two teams looking to return to former glories, a Derby della Madonnina that the world will stop to watch.
Despite the rivalry between the sides, several stars have adorned the colours of both clubs. Such has been the level of talent have represented both, the likes of Patrick Vieira, Edgar Davids, Christian Vieri and Hernan Crespo all fail to make this list.
Here are five of the best players to play for Inter and AC Milan.
One of the greatest footballers Italian football has ever produced, the former World Player of the Year and Ballon d’Or winner enjoyed the best period of his career at Juventus, though would represent both Milan clubs following his departure from the Turin side.
Squeezed out at Juve following the emergence of a young Alessandro del Piero, Baggio made a £6.8m transfer to divisional rivals AC Milan in 1995 and inspired the Rossoneri to the Serie A title ahead of his former side, before being named as the club’s Player of the Season.
⚽ Goal of the Day 💥
Roberto Baggio freezes the keeper with free-kick magic ✨ Hats off 🎩
Palla nel 7⃣: il “Divin Codino” dipinge calcio 🎨🖌 pic.twitter.com/VKeppGW28B
— AC Milan (@acmilan) June 10, 2018
His creative talents also saw him provide the most assists in Italy’s top-flight alongside his ten goals in all competitions, though after an initial bright start at the San Siro – becoming one of six players to win the Scudetto in consecutive years with different teams – he fell out-of-favour and joined Bologna.
Following a renaissance at Bologna in which he scored a career-best 22 league goals in his single season at the club, Baggio returned to Milan in the colours of Inter – the club he had supported as a boy.
Despite scoring 17 goals in 59 appearances over two seasons, his time was marred by injuries and he failed to win silverware with the club before ending his illustrious career with Brescia.
90s Hitmen: The Divine Ponytail, Roberto Baggio
An irrepressible talent at his mesmerising peak, Ronaldo – or Ó Fenómeno as he would come to be known – arrived at Inter Milan in a world record deal in 1997. Such had been his early impact, the Brazilian star became the most expensive player in football history twice before his 21st birthday.
Having burst onto the European scene with a prolific spell at PSV Eindhoven, Ronaldo starred during a breathtaking individual season at Barcelona. His 47-goal campaign for the Spanish side persuaded Inter to part with a record sum to sign the forward.
A powerful runner with dazzling footwork and pinpoint precision finishing, Ronaldo was simply devastating at the peak of powers and arguably the finest out-and-out centre-forward the game has seen.
His arrival at the San Siro was supposed to herald a new dawn as Inter looked to wrestle supremacy back from the Milan and Juventus sides that had dominated the nineties. Ronaldo began brilliantly with goal after goal and retained the FIFA World Player of the Year award in 1997 after becoming the youngest recipient of the award the previous year.
The Ballon d’Or followed, Ronaldo again the youngest winner of the award, after a season which saw the Brazilian lead Inter to UEFA Cup success. However, disaster soon struck as injuries began to take their toll and his career was placed in doubt.
Ronaldo ruptured the tendon in his right knee against Lecce in 1999 and rushed back to feature as a substitute for the Coppa Italia final. He lasted just seven minutes before clutching his knee once again in agony and barely featured over the next three seasons following a succession of injuries.
He rose again and won the World Cup with Brazil in 2002 to win a second Ballon d’Or, before moving to Real Madrid as part of the club’s Galacticos project. After a prolific spell in Spain, he returned to Serie A to sign for AC Milan. His second stint in the division brought just nine goals in 20 appearances however, with Ronaldo’s powers on the decline.
Which of O Fenômeno’s goals has you off your seat? ⚽️#SempreMilan pic.twitter.com/yYOYlNETLF
— AC Milan (@acmilan) March 25, 2023
Ronaldo was an exhilarating talent whose brilliant best was at a level that has rarely been seen before or since, though there is a sense of what might have been for both Inter and Ronaldo had injury not struck.
Having began his career as an attacking midfield player, Pirlo’s performances for hometown club Brescia attracted the interest of Inter Milan. The Nerazzurri agreed a deal to bring the young star to the San Siro, though it proved a frustrating period in the developing playmaker’s career.
Having failed to cement himself as a regular at Inter, Pirlo spent time on loan at Reggina and former club Brescia, where he was utilised in a deeper position at the latter in a move which would transform his fortunes.
Despite impressing out on loan, Inter sold Pirlo to city rivals AC Milan. It remains a deal of regret, with Pirlo fulfilling his potential in the red and black colours of the club’s city rivals. Sitting in front of the defence, he developed a reputation as one of the best deep-lying playmakers and set-piece takers in world football.
His effortless brilliance helped deliver two Serie A titles and two Champions League trophies during a glittering period under Carlo Ancelotti, all achieved with nonchalant style and swagger.
🇮🇹 The ‘Professor’ Andrea Pirlo = football genius 😎 #UCL | @Pirlo_official pic.twitter.com/rUzLvaPKYr
— UEFA Champions League (@ChampionsLeague) May 1, 2020
After 401 appearances and 41 goals he was inexplicably allowed to leave for Juventus on a free transfer, a decision Milan – like Inter before them – came to regret. Pirlo inspired the Old Lady to four consecutive league titles and was named as Serie A Footballer of the Year in three successive seasons.
Midfield Magicians: The Architect, Andrea Pirlo
Another player who formed part of Carlo Ancelotti’s all-conquering AC Milan side, Seedorf had won Champions League titles at Ajax and Real Madrid before first joining Inter Milan in 1999.
The Dutch international spent three seasons in the famed blue and black, though failed to win silverware with the club during that period, with a Coppa Italia final defeat the closest the midfielder came to success.
Part of a memorable trade deal between the two Milan clubs in 2001, Seedorf headed to the Rossoneri in exchange for highly-rated defender Francesco Coco and it would be his new side who got the better end of the bargain.
🇳🇱 Seedorf was elite 🔝#UCL pic.twitter.com/NnQPoqP0P5
— UEFA Champions League (@ChampionsLeague) April 1, 2023
Seedorf helped Milan end a 26-year wait for a Coppa Italia triumph in 2003, before impressing as Ancelotti’s side secured Champions League glory that same season. Milan defeated Juventus on penalties in the first ever all-Italian final as Seedorf became the first footballer to lift the trophy with three different clubs.
Two Serie A titles and another Champions League were later won during a decade at the club that delivered ten trophies. The Dutchman left the club for Brazilian side Botafogo having scored 63 goals in 431 appearances and later returned for a short spell as manager.
Midfield Magicians: A bona fide winner who simply oozed class, Clarence Seedorf
Zlatan Ibrahimovic has arguably enjoyed the greatest successes on either side of the divide, having scored prolifically for both teams and won Serie A titles in the colours of both Inter and AC Milan.
Having starred during two seasons at Juventus, Ibrahimovic left the Turin side following their relegation due to the Calciopoli scandal and moved to divisional rivals Inter alongside teammate Patrick Vieira.
His first season at the club delivered 15 goals and Scudetto success, as Inter won the title with a record 97 points. The Swede scored prolifically across the following two seasons as the Nerazzurri won three Serie A titles in succession.
His influence was rewarded with Serie A Footballer of the Year and Foreign Footballer of the Year accolades in successive seasons, the latter of which also saw him win the Capocannoniere award as Italian football’s leading scorer
Following an ill-fated season in Spain following a record-breaking move to Barcelona, Ibrahimovic returned to Serie A at AC Milan, initially on loan before signing on a permanent basis.
He scored 56 goals in just 86 appearances and was named as Serie A Footballer of the Year for a third time after firing the club to the league title in 2011. He won another Capocannoniere award the following season after a 28-goal haul.
After spells with Paris Saint-Germain, Manchester United and LA Galaxy, he is now back in the red and black stripes seeking to create more history. He has scored 37 goals in 78 appearances during his second spell at Milan and became Serie A’s oldest ever goalscorer in March 2023, aged 41 years and 166 days.
Read – Five of the best Serie A strikers of the 90s
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