AIM: To evaluate outcomes and determine factors influencing the outcomes of vitrectomy with silicone oil (SO) endotamponade for the management of rhegmatogenous retinal detachment (RRD) complicated by advanced proliferative vitreoretinopathy (PVR). METHODS: This is a retrospective, interventional case series of eyes with PVR grade C associated RRD with or without prior surgery that underwent vitreoretinal surgery and SO tamponade. Eyes with a minimum follow-up of 6mo after SO extraction were included. Eyes were classified into three PVR subgroups according to severity and extension of proliferation. The influence of several preoperative, intraoperative and postoperative factors upon the functional and anatomical outcomes was assessed using multivariate logistic regression analysis. RESULTS: A hundred and one eyes of 101 patients that met the inclusion criteria were studied. Seventy-five of 101 eyes (74.3%) had successful retinal reattachment after one operation. Increased aqueous cell and flare at the first week exam had a statistically significant association with redetachment, recurrent membrane proliferation and keratopathy. Visual acuity improvement was significantly associated with faint postoperative aqueous inflammation values, primary vitrectomy and PVR outside of the posterior pole. CONCLUSION: Although encouraging anatomical and functional outcomes are achieved after vitrectomy and SO tamponade in eyes with RRD complicated by PVR, an increase in aqueous flare or cells at the first week follow-up is most likely to result in postoperative late complications. Primary vitrectomy, PVR associated with minimal posterior pole extension and absent to mild postoperative aqueous inflammation are associated with improved post-operative final visual acuity.