To present ocular features associated with surgical outcomes in infants with stages 4 and 5 retinopathy of prematurity (ROP). Twenty-two infants (35 eyes) were referred for vitreoretinal surgery for stages 4 and 5 ROP. The following ocular features recorded before the development of retinal detachment requiring surgical intervention were analyzed: clock hour extent of ridge elevation, vitreous state, plus disease, prominent iris vessels, neovascularization, and the presence of exudates. Surgical procedures included scleral buckle, lensectomy-vitrectomy, and lens-sparing vitrectomy. Univariate and multivariate analyses were used to determine features associated with failure to achieve retinal reattachment as the main outcome variable. Of the 35 eyes that underwent at least one surgical procedure, nine had successful retinal reattachment after the first surgery, and 18 achieved it at the end of follow-up. After accounting for the correlation between the eyes, features significantly associated with surgical failure after the first surgery were vitreous haze, hemorrhage, or organization; plus disease; and neovascularization. The presence of exudates was significantly associated with a successful outcome. When eyes were analyzed by stage at the first procedure, vitreous organization and plus disease were associated with failed retinal reattachment in stage 4 eyes, whereas at least 6 clock hours of ridge elevation and plus disease were significant in stage 5 eyes. The need to perform a lensectomy-vitrectomy was associated with a poor surgical outcome. Neither stage nor number of procedures performed was associated with the development of phthisis. Vitreous haze, neovascularization, and plus disease are associated with a poor surgical outcome in eyes that progress after treatment for threshold ROP requiring surgical intervention for retinal detachment. When eyes were divided by stage of ROP at first surgery, plus disease remained a significant variable associated with failed retinal reattachment. Close observation of eyes after laser treatment for threshold ROP is necessary. If neovascularization and plus disease persist and progression of ROP is noted, additional laser should be considered before surgery for retinal detachment. Additional studies with a larger patient sample will be necessary to further define ocular features associated with surgical outcome for ROP.