Several iconic players have crossed the divide, cementing their place in the history of both clubs:

A legendary playmaker for both, spending seven seasons at Fiorentina and five at AC Milan.

The "Divine Ponytail" represented both clubs during his illustrious career.

AC Milan's biggest win against "La Viola" was a dominant 6–0 victory in 2004, while Fiorentina’s most notable high-scoring win recently was a 4–3 thriller in November 2021.

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