Purpose <p>To evaluate the incidence, timing, predictive factors, pathophysiological mechanisms, and management outcomes of recurrent vitreous hemorrhage (RVH) following pars plana vitrectomy (PPV) in patients with advanced proliferative diabetic retinopathy (PDR), and to contextualize these findings within the current literature.</p> Methods <p>This retrospective cohort study included 65 patients undergoing 25-gauge PPV for vitreous hemorrhage secondary to PDR with a mean follow-up of 15 ± 3 months. All patients received preoperative anti-VEGF injection 5 days prior to surgery. Demographic, systemic, ocular, and intraoperative variables were analyzed. Recurrent vitreous hemorrhage was classified as early (&lt; 4 weeks) or late (&gt; 4 weeks). Comparative univariate analyses were performed to identify factors associated with RVH.</p> Results <p>Recurrent vitreous hemorrhage developed in 13 of 65 patients (20.0%). Early RVH occurred in 11 patients (16.9%), whereas late RVH occurred in 2 patients (3.1%). Severe intraoperative bleeding (38.5% vs. 0%, <i>p</i> &lt; 0.001), anticoagulant use (53.8% vs. 25.0%, <i>p</i> = 0.04), and dialysis (38.5% vs. 9.6%, <i>p</i> = 0.01) were significantly associated with RVH. Silicone oil tamponade was less frequently used in patients who developed RVH (23.1% vs. 65.4%, <i>p</i> = 0.01). Tractional retinal detachment was not significantly associated with RVH (<i>p</i> = 0.78).</p> Conclusion <p>Recurrent vitreous hemorrhage remains a clinically significant complication following PPV in advanced PDR. Severe intraoperative bleeding, anticoagulant use, and dialysis were significantly associated with RVH development, whereas silicone oil tamponade was associated with a lower frequency of postoperative hemorrhage. These findings may contribute to risk stratification and postoperative monitoring in patients with advanced PDR.</p>