The purposes of this case-control study (N=20) were to examine the effects of IAT and tendon region on tendon strain in patients with insertional Achilles tendinopathy (IAT) compared to a control group without tendinopathy. An ultrasound transducer was positioned over the Achilles tendon insertion during dorsiflexion tasks, which included standing and partial squat. A non-rigid image registration-based algorithm was used to estimate transverse compressive and axial tensile strains of the tendon from radiofrequency ultrasound images, which was segmented into two regions (superficial tendon and deep). For transverse compressive strain, two-way mixed effects ANOVAs demonstrated that there were interaction effects between group and tendon region for both dorsiflexion tasks (Heel lowering, P= 0.004; Partial squat, P= 0.008). For axial tensile strain, the IAT group demonstrated a main effect of lower tensile strain than the control group (Standing, P=0.001; Partial squat, P=0.033). There was also a main effect of greater tensile strain in the superficial region of the tendon compared to the deep during standing (P=0.002), but not during partial squat (P=0.603). Reduced transverse compressive and axial tensile strains in the IAT group indicate altered mechanical properties specific to the region of IAT pathology. Additionally, patterns of compressive strain are consistent with the theory of calcaneal impingement contributing to IAT pathology.