Purpose: To describe the surgical outcomes of rhegmatogenous retinal detachments (RRDs) associated with giant retinal tears (GRTs) and define factors associated with primary anatomic failure. Methods: This retrospective consecutive study comprised primary GRT-RRD surgeries between 1999 and 2021 at a single institution. Exclusion criteria were a follow-up of less than 3 months and incomplete surgical data. Results: The series included 69 eyes (64 patients). Single-surgery anatomic success (SSAS) was achieved in 75% and final anatomic success (FAS) in 90%. The mean logMAR visual acuity improved from 1.5 ± 1.1 to 0.6 ± 0.9. Preoperative factors significantly associated with redetachment were proliferative vitreoretinopathy (PVR) (odds ratio [OR], 6.2; P < .01), hypotony (OR, 13.6; P < .01), and a 180-degree or larger GRT (OR, 3.3; P = .04). All cases were treated with pars plana vitrectomy (PPV) and perfluoro-N-octane (PFCL). Perfluoropropane (C3F8) was used in 59% and silicone oil in 41%; the redetachment rate was significantly lower in gas cases (15% vs 39%) ( P = .02). An encircling band, placed in 84% eyes, had a tendency to reduce redetachment (22% vs 36%) ( P = .32). Lensectomy was performed in 61% of phakic eyes, with no effect on redetachment (20% vs 21%) ( P = .92). On multivariate analysis, PVR and hypotony were significantly associated with redetachment. Conclusions: PPV with PFCL achieved high SSAS and FAS rates. PVR and hypotony were the main preoperative factors associated with anatomic failure. In cases without PVR, C3F8 tamponade significantly increased SSAS. Encircling scleral buckling showed a nonsignificant tendency toward an increase in SSAS. Lensectomy had no effect on SSAS.