Throughout the preparation, enactment, and chronicling of ceremonial entries during the Italian Wars (1494–1559), cities and their entrants utilized gendered performance and allegory to articulate and negotiate their political relationships. The northern coastal republic of Genoa was a pivotal ally, first for Valois, and then for Habsburg rulers, and was consequently the stage for both triumphant entries and entries-in-arms. By examining the entries of King Louis XII of France, Holy Roman Emperor Charles V, and his son Prince Philip of Spain, this study will demonstrate Genoa’s flexibility of gendered self-representation and its subjection to foreign interpretation. The city and entrants communicated their desired political dynamics through their interactions, which reflected gendered social dynamics. Likewise, political interpreters, be they organizers tasked with staging an entry or poets tasked with shaping its cultural memory, drew upon gendered scenarios from kinship, classical, and literary traditions to place the city in relation to the entrant.