The Contrada del Drago was among the first to appear in public celebrations on the Campo. Along with Giraffa, Chiocciola, and Onda, it participated in a "Pugna," organized in honor of Cardinal St. Malò on March 1, 1494. Results from recent research document its existence as early as 1481, and significantly, outside of participation in public events. The Contrada includes the ancient Military Companies of San Donato da’ Montanini and Sant’Egidio del Poggio Malavolti. It probably took its emblem and name from the mythical animal depicted on the crest of the former. Some believe instead that the name and emblem could derive from the Borghesi family's coat of arms: a yellow dragon on a green field, while others think it might have adopted the emblem from the Benincasa's family, the family of Saint Catherine, who is also its Patron Saint. In any case, it was with a dragon-shaped machine that the members of this Contrada participated in the first "Bull Hunts" and were called "the men of the Dragon."

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