The objective of this study was to demonstrate the effect of intravenous (IV) zoledronate administration on rotator cuff healing, retear rate, and clinical outcomes in osteoporotic patients who underwent arthroscopic rotator cuff repair (ARCR) compared with patients with normal bone densities. In this prospective nonrandomized comparative study with propensity score matching, 30 patients who were postoperatively administered IV zoledronate (5 mg) were enrolled as the study group. The control group was matched using 1-to-2 propensity score matching. Radiologic and functional outcomes were evaluated 6 months after surgery. The functional scores in both groups exhibited significant improvement 6 months after surgery. Compared with Group 1 (osteoporosis with IV zoledronate injection) Group 2 (normal bone density) showed significant improvement in their University of California, Los Angeles (UCLA) shoulder score and Constant Shoulder Score (CSS) at 6 months postoperatively. The range of motion improved in both groups at 6 months after surgery. The retear rates according to Sugaya's classification (IV and V) were 13.3% (4 of 30 patients) and 25% (15 of 60 patients) in Groups 1 and 2, respectively, which established a non-inferiority of Group 1 to the control group. The retear pattern according to Rhee's classification in Group 1 was type I in all cases, whereas eight cases of type I and seven cases of type II patterns were observed in Group 2, which was statistically insignificant between the groups. In conclusion, anti-osteoporotic drug use is beneficial for patients with osteoporosis to reduce the failure rate after an ARCR of length > 2 cm, especially in older female patients. Moreover, thorough scrutiny is required to detect osteoporosis in patients with rotator cuff tears, especially in female patients.