Metatarsal stress fractures are common overuse injuries in athletes, military recruits, and ballet dancers, usually occurring in the second, third, and fourth metatarsals, respectively. Such fractures may also occur in a variety of other individuals, regardless of demographic characteristics, sex, or profession, and they are highly associated with excessive activity. Moreover, these types of fractures are usually diagnosed late and have poor outcomes. To our knowledge, there has been only one case report of an individual with stress fractures of all three central metatarsals in the same foot. We describe herein a racehorse training jockey who presented with multiple simultaneous metatarsal stress fractures in the same foot. We also discuss the possible mechanisms by which this entity occurred, as well as its management and outcome.