The season began with three matches in the first round of the Coppa Italia, where Milan, in group 3 with Varese, Verona and Como, gets two draws against Varese and Verona and a victory against Como. The four points in the standings are not enough to qualify for the next round, which Varese enters by scoring one goal more than the Rossoneri.
In October 1969, Milan won the Intercontinental Cup, the first in the club's history. In the first leg at San Siro, Milan beat the Argentines of Estudiantes with the score of 3–0, thanks to a brace from Sormani and a goal from Combin. The return match was played in Buenos Aires and was characterized by the highly aggressive play of the Argentine team; to pay the highest price were Prati, who was hit in the back and forced to leave the field after 37 minutes of play, and above all Combin, who left the pitch with the fracture of his nose and cheekbone. The final result of the match is 2–1 for the Argentines, who overturned Rivera's goal with those from Conigliaro and Aguirre Suárez, but the narrow defeat still allows Milan to win the trophy. After the match, the behavior of the Argentine players lead to the life ban of goalkeeper Poletti (subsequently revoked) and the long suspensions of Aguirre Suárez and Manera by the Argentine Federation as well as the imprisonment of the three for 30 days.[2][3][4]
In the European Cup, Milan, after eliminating Luxembourg's Avenir Beggen in the round of 32 in September (5–0 at home and 3–0 away), were eliminated in the round of 16 by Dutch side Feyenoord who overturned the 1–0 defeat in the first leg in Milan thanks to the 2–0 obtained in Rotterdam.
In the Serie A, Milan remained permanently in the top positions finished in 4th place with 36 points, nine points behind Scudetto winner Cagliari, five from Inter and two from Juventus: however, this result would be insufficient for the purposes of qualifying for the European Cups given that the "one city, one team" rule of the Inter-Cities Fairs Cup barred access to the Rossoneri in favor of Inter, who preceded Milan in the final league standings.
During the season, AC Milan captain Gianni Rivera was awarded the 1969 Ballon d'Or, thus becoming the first Italian to receive this recognition.
Squad
Note: Flags indicate national team as defined under FIFA eligibility rules; some limited exceptions apply. Players may hold more than one non-FIFA nationality.
