To analyze the rate and timing of retinal redetachments and other complications following pars plana vitrectomy for retinal detachment repair with silicone oil tamponade and the effect of face-down positioning duration on these endpoints. A retrospective study was performed on patients with retinal detachment repair via pars plana vitrectomy with silicone oil tamponade between 2015 and 2020. Surgery was performed by 10 physicians associated with a private retina practice in Cleveland, Ohio. Duration of postoperative face-down positioning was noted and patients were grouped by short (≤6 days) or long (≥7 days) durations. Outcome variables were retinal re-detachment, epiretinal membrane formation, cataract formation, and other complications. Timing and frequency of outcomes were noted and statistical analysis was performed. The study was composed of 227 eyes. The mean age of patients was 62.09±13.65 years with 143 (63.00%) male and 84 (37.00%) female. Of the initial detachments, 63 (27.88%) were macula-on and 163 (72.12%) were macula-off. Overall, 128 (56.39%) patients were given instructions for face-down positioning for 6 days or less and 99 (43.61%) patients for 7 days or more. Retinal redetachment was seen in 42.19% of patients with face-down positioning ≤6 days and 29.29% of patients with face-down positioning ≥7 days (P = .045). No significant difference was found in epiretinal membrane formation or cataract formation (P >.05). There was a lower rate of redetachment in patients who kept a face-down position for ≥7 days compared with ≤6 days. Further study to determine causality between duration of postoperative face-down positioning and retinal redetachment is recommended. [Ophthalmic Surg Lasers Imaging Retina. 2022;53:285-292.].