The competition between fracture modes in monolithic brittle materials loaded in cyclic contact in aqueous environments with curved indenters is examined. Three main modes are identified: conventional outer cone cracks, which form outside the maximum contact; inner cone cracks, which form within the contact; and median–radial cracking, which form below the contact. Relations describing short-crack initiation and long-crack propagation stages as a function of number of cycles, based on slow crack growth within the Hertzian field, are presented. Superposed mechanical driving forces—hydraulic pumping in the case of inner cone cracks and quasiplasticity in the case of median–radials—are recognized as critically important modifying elements in the initial and intermediate crack growth. Ultimately, at large numbers of cycles, the cracks enter the far field and tend asymptotically to a simple, common relation for center-loaded pennylike configurations driven by slow crack growth. Crack growth data illustrating each mode are obtained for thick soda-lime glass plates indented with tungsten carbide spheres in cyclic loading in water, for a range of maximum contact loads and sphere radii. Generally in the glass, outer cone cracks form first but are subsequently outgrown in depth as cycling proceeds by inner cones and, especially, radial cracks. The latter two crack types are considered especially dangerous in biomechanical applications (dental crowns, hip replacements) where ceramic layers of finite thickness are used as load-bearing components. The roles of test variables (contact load, sphere radius) and material properties (hardness, modulus, toughness) in determining the relative importance of each fracture mode are discussed.