The purpose of this histologic study was to identify the most effective bony surface for fibrous connection to bone after immediate repair of the canine infraspinatus. Light microscopic views were used to evaluate collagen fiber development. The left infraspinatus tendon of 15 dogs was transected and repaired to 3 different bone surfaces: a tendon end adjacent to the tendon insertion (group 1, n = 5), a calcified fibrocartilage layer (group 2, n = 5), and a cancellous surface (group 3, n = 5). Tendon repair to distal tendon ends restored the 4-layered enthesis in the healing period, whereas tendon repair to the calcified fibrocartilage layer considerably delayed fiber development into bone. Fiber connection to cancellous surface developed according to the remodeling of trabecular bone. Secure fiber connection into the thickened trabecular bone developed by 16 postoperative weeks. On the basis of these results, in clinical settings, ruptured tendon ends should be attached to the remaining distal tendon end or to a cancellous surface; they should not be attached to a calcified fibrocartilage layer.