Consideration is given to the two major military saints to be associated with dragon fights, Theodore Tyron and George. In contrast to the majority of their saintly peers, they fight their dragons in a duly martial fashion. However, within the span of their narratives, the physical fight itself is typically brief, desultory, and anticlimactic, a coda to a more spiritual battle that has already been won. The two saints’ traditions are contexualized in different ways. The structure and motifs of a fourteenth-century AD account of Theodore’s fight against the Dragon of King Samuel’s City is aligned with those of the dragon fight of a roughly contemporary Byzantine romance, Callimachus and Chrysorrhoe. Whilst the earliest extant narrative of George’s fight against his dragon is relatively late, eleventh-century AD, what today survives as the principal living relic of his dragon-fight, its iconography, can be shown to have its roots in the very beginning of classical antiquity.