Tendons are bradytrophic tissues, characterized by a dense extracellular matrix in their core, low cellularity, and limited vascularization under healthy conditions. Upon sustaining injury or undergoing degenerative changes, matrix quality decreases and generally a hypervascular, fibrotic scar tissue forms. The significance of angiogenesis in this context remains a topic of ongoing debate and investigation. This review focuses on the vasculature of healthy tendon tissue and the angiogenic mechanisms involved in tendinopathy, with a particular emphasis on Achilles tendon tendinopathy. Furthermore, this narrative review discusses the ongoing controversy surrounding the potential benefits of either promoting or limiting vascular supply in tendon healing.