We examine the relationship between age, sickness, and longevity among men who were members of the Hampshire Friendly Society (HFS) in southern England during the late nineteenth and the early twentieth centuries. The HFS insured its members against sickness, death, and old age, keeping detailed records of the claims for sick pay submitted by its members from 1868 onward. From 1892 onward these records included information about the cause of the sickness for which compensation was paid. We can therefore use this information to construct individual “sickness biographies” for men who joined the society during this period. This article uses these sickness histories to address two questions. The first concerns the relationship between the age of the society’s members and the nature of the claims they submitted. We find that both the incidence and the duration of periods of sickness increased with age. Older men experienced longer periods of sickness both because they experienced different types of sickness and because it took them longer to recover from the same illnesses as those suffered by younger men. The second question is whether sickness in early adulthood was associated with increased mortality. We find that repeated bouts of sickness, as revealed by the number of claims made for sick pay, at ages under 50 years were associated with an increased risk of death at ages over 50 years.