The structural evolution upon high-cycle fatigue (tension with the magnitude of stress in a cycle below the macroscopic yield stress) of the hypereutectoid steel U10 (1.03 wt % C), in which pearlite of different morphology (fine-lamellar, coarse-lamellar, and partially spheroidized pearlite) was formed, has been investigated by scanning and transmission electron microscopy. Based on the fractographic analysis, features of fracture of these structural states have been considered. At a significant distance (10 mm) from the fatigue fracture, features of structural transformations caused by cyclic loading have been revealed. It has been shown that upon high-cycle fatigue in the steel U10 with structures of lamellar and partially spheroidized pearlite, substantial structural changes occur, namely, fragmentation and partial dissolution of cementite plates, and in fine pearlite, additionally, spheroidizing of cementite and polygonization of the ferritic component are observed. A dependence of the character of fracture on the type of structure formed upon fatigue loading has been established. In the steel with a nonequilibrium structure of unannealed fine pearlite, an enhanced elasticity modulus, as compared to other more stable structures (coarse-lamellar, annealed fine, and spheroidized pearlite), and a reduction in the magnitude of the elasticity modulus under the action of cyclic loading have been found. It has been established that the structural changes in fine pearlite of laboratory specimens of the steel U10 upon cyclic tension are qualitatively similar to those in a railroad wheel of the steel 65G under the service conditions.