Background: Pertrochanteric calcifications can be found in patients with greater trochanteric pain syndrome (GTPS). A systematic description of the types and prevalence of these calcifications has not been undertaken. Furthermore, there is conflicting evidence regarding their association with abductor tendon injuries. Purpose: (1) To describe the various types and prevalence of pertrochanteric calcifications in patients presenting for the surgical management of recalcitrant GTPS. (2) To evaluate the association of the various calcifications with intraoperatively diagnosed hip abductor tendon injuries, including tendinosis, partial-thickness tears, and full-thickness tears. Study Design: Cross-sectional study; Level of evidence, 3. Methods: Patients undergoing surgical management for GTPS, in isolation or as an ancillary procedure during hip arthroscopy for femoroacetabular impingement, between April 2008 and February 2020 were included. Of these, 85 procedures were isolated treatment of GTPS and the remaining 628 were ancillary to hip arthroscopy. Radiographs were scrutinized for the presence of pertrochanteric calcifications. The hip abductor tendon status was intraoperatively classified as intact, partial-thickness tear, or full-thickness tear. The prevalence and correlation of the various radiographic findings in relation to the intraoperatively classified tendon condition were analyzed via the odds ratio (OR). Results: Surgery was performed on 713 hips with recalcitrant GTPS. No tear was found in 340 hips (47.7%), 289 hips (40.5%) had a partial-thickness tear, and 84 hips (11.8%) had a full-thickness tear. Radiographically, 102 hips (14.3%) demonstrated proximally directed enthesophytes, and 34 (4.8%) had distally directed enthesophytes. In addition, 75 hips (10.5%) had amorphous calcifications, 47 (6.6%) had isolated ossicles, and 110 (15.4%) had surface irregularities. The presence of any calcification was associated with partial-thickness tears (OR, 1.67 [95% CI, 1.21-2.21]; P = .002) and full-thickness tears (OR, 6.40 [95% CI, 3.91-10.47]; P < .001). Distally directed enthesophytes (OR, 10.18 [95% CI, 3.08-33.63]; P < .001) and proximally directed enthesophytes (OR, 8.69 [95% CI, 4.66-16.21]; P < .001) were the findings with the highest OR for the presence of any type of tear. Distally directed enthesophytes were the findings with the highest OR for a full-thickness tear (OR, 15.79 [95% CI, 7.55-33.06]; P < .001). Isolated ossicles were the findings with the highest OR for a partial-thickness tear (OR, 1.73 [95% CI, 0.96-3.13]; P = .070). Conclusion: Pertrochanteric calcifications were common radiographic findings in patients with GTPS and can help guide management in these patients. Proximally and distally directed enthesophytes were strong predictors for the presence of a hip abductor tendon tear, and specifically a full-thickness tear, and increasing size of the findings was associated with more severe tendon injuries.