Purpose: To evaluate functional and anatomical outcomes of patients with retinal redetachments (re-RD) after surgery for primary rhegmatogenous retinal detachment. Methods: Medical records of eyes with re-RD after rhegmatogenous retinal detachment surgery between 1999 and 2014 at the Department of Ophthalmology, University of Cologne, Germany, were retrospectively evaluated. Data included preoperative and postoperative clinical findings, best-corrected visual acuity, presence and grade of proliferative vitreoretinopathy, surgical procedures, and complication rates. Results: Three hundred and twenty-eight eyes of 2,457 developed a re-RD (13.3%). Of these 328 eyes, 242 eyes (73.8%) had only one re-RD, whereas 86 eyes (26.2%) had 2 or more re-RDs. Visible presence of proliferative vitreoretinopathy during first redetachment surgery increased risk of re-RD with relative risk ratio of 1.46 (P = 0.05). Best-corrected visual acuity deteriorated with every additional re-RD (P < 0.001). Two hundred and thirty-seven eyes received oil endotamponde at least once. In 91 cases, oil endotamponade was left for long-term until last follow-up. Conclusion: Multiple re-RD (>= 2 re-RDs) is an infrequent complication after rhegmatogenous retinal detachment surgery. After a first re-RD occurred, risk for multiple re-RD doubles compared with the risk of a first redetachment. Mean functional outcome is unfavorable, whereas predictability remains nevertheless poor because of the wide range of interindividual postoperative best-corrected visual acuity.