The major muscular prime movers and stabilizers of the foot and ankle originate in the mid to lower leg and send their tendons distally. Most of these tendons, with the exception of the Achilles and plantaris tendons, must negotiate a sharply curved course at the ankle and are stabilized by fibro-osseous tunnels, pulleys, or fibrous retinaculi before eventually inserting at the foot. Knowledge of specific tendon anatomy, contact points and sites of physical and vascular stress, helps to identify those regions susceptible to degeneration or tearing and to optimize the design of imaging protocols. This review covers the imaging modalities used to assess tendons about the ankle and issues related to their usage, normal tendon structure and relevant anatomy, normal imaging appearances and artifacts, and the common degenerative pathological processes which imaging can show.