On June 14, 1988, the San Siro witnessed the birth of a new tradition as AC Milan faced Sampdoria in the inaugural Italian Super Cup. The match pitted Serie A champions Milan—boasting legends like Ruud Gullit and Marco van Basten—against Coppa Italia winners Sampdoria, led by Roberto Mancini and Gianluca Vialli.
Sampdoria struck first through Vialli’s 14th-minute finish, but Milan’s "Invincibles" era began in earnest with a resounding comeback. Frank Rijkaard equalized just four minutes later, before substitute Mauro Mannari and Van Basten (from the spot) sealed a 3-1 victory. The triumph marked the start of Milan’s dominance under Arrigo Sacchi, who would lead them to two European Cups and three Serie A titles. The Super Cup quickly became a showcase for Italy’s top clubs, blending competitive intensity with glamour—a legacy still alive today.
