Purpose The goal of this study was to identify risk factors for redetachment and/or a worse visual outcome after silicone oil removal (SOR) for complicated retinal detachment. Methods The authors retrospectively analyzed 287 consecutive eyes with SOR between January 1999 and December 2003. Results Anatomic success after SOR was achieved in 81% of the eyes. The overall anatomic success at the end of follow-up was 94%. Postoperative ocular hypertension was found in 8% of the eyes, hypotony in 6% of the eyes, and keratopathy in 29% of the eyes. After SOR 43% of the eyes had an improvement in visual acuity of at least two Snellen lines. After multivariate analysis, male sex, the presence of preoperative rubeosis, and proliferative diabetic retinopathy (PDR) were found to be risk factors for recurrent retinal detachment. Male sex, preoperative visual acuity of <0.1 Snellen lines, PDR, the performance of three more operations, any size of retinectomy, and hypotony were found to be associated with a poor visual outcome of Snellen visual acuity <0.1. Conclusions Retinal detachment after SOR in the current unselected series of eyes occurred in approximately 20%, which is comparable to the Silicone Oil Study reports, published approximately 20 years ago. However, preoperative selection was then made, and less than 50% of the silicone oil-filled eyes had SOR. The higher overall anatomic success in the current study may be due to improved vitreoretinal surgical techniques.