Background: Although previous studies have reported acceptable clinical outcomes after simultaneous, single-stage bilateral and staged bilateral rotator cuff repair (RCR), few studies have been adequately powered to compare postoperative complication rates at various time intervals between procedures. Purpose: To examine the relationship between the timing of bilateral arthroscopic RCR and complications. Study Design: Descriptive epidemiology study. Methods: Patients from the Medicare data set within the PearlDiver database who underwent bilateral RCR between 2005 and 2014 were identified. These patients were then stratified by time between surgeries into cohorts: (1) single stage, (2) <3 months, (3) 3 to 6 months, (4) 6 to 9 months, (5) 9 months to 1 year, and (6) 1 to 2 years. Surgical and medical complications of these cohorts were compared with those of a control cohort of patients who underwent bilateral RCR >2 years apart using a regression analysis. Results: A total of 11,079 patients who underwent bilateral RCR were identified. Patients who underwent single-stage bilateral arthroscopic RCR experienced higher rates of revision RCR (odds ratio [OR], 2.1; P < .0001), reverse total shoulder arthroplasty (RTSA) (OR, 2.47; P < .0001), and postoperative infection (OR, 2.18; P = .007) in addition to higher rates of venous thromboembolism (VTE) (OR, 1.78; P = .031) and emergency department visits (OR, 1.51; P = .002) compared with the control group. Patients who underwent bilateral RCR with a <3-month interval had higher rates of revision surgery (OR, 1.56; P = .003), RTSA (OR, 1.89; P = .002), and lysis of adhesions (OR, 2.31; P < .0001) in addition to increased rates of VTE (OR, 1.92; P = .015) and emergency department visits (OR, 1.62; P < .0001) compared with the control group. There were no differences in any surgical or medical complications when surgeries were staged by ≥3 months compared with controls. Conclusion: Patients with Medicare undergoing single-stage and staged bilateral RCR who had the second repair within 3 months had significantly higher rates of multiple medical and surgical complications compared with patients waiting >2 years between procedures.