Vitreoretinal surgery often achieves anatomical success; however, functional recovery differs markedly among eyes with similar disease presentations. Retinal imaging biomarkers help reduce this uncertainty by characterizing tissue composition, photoreceptor integrity, traction, perfusion, inflammation, and postoperative remodeling before these changes are evident in visual acuity. This structured review compiles evidence from 2020 to 2025 regarding optical coherence tomography, optical coherence tomography angiography, wide-field imaging, fundus autofluorescence, and emerging computational evaluations for predicting outcomes after surgery for epiretinal membrane, macular hole, rhegmatogenous retinal detachment, and tractional diabetic retinal disease. A translational framework is used, distinguishing preoperative risk stratification, intraoperative confirmation, early postoperative assessment, and longitudinal recovery. Across indications, the most consistent favorable prognostic indicators include preserved ellipsoid-zone and external-limiting-membrane continuity, limited inner retinal disorganization, reduced chronicity-related tissue deformation, smaller or more favorable lesion geometry, and early restoration of normal foveal architecture. In contrast, ectopic inner foveal layers, extensive disorganization of retinal inner layers, persistent subretinal fluid, outer retinal corrugation, hyperreflective inflammatory deposits, severe macular ischemia, and segmentation-unstable edema are associated with slower or incomplete recovery. No single metric demonstrates sufficient robustness across diseases, devices, and surgical techniques. The most effective prognostic approach merges with structural condition, lesion geometry, perfusion, symptom-relevant function, and temporal change. Standardized acquisition, masked grading, artifact reporting, external validation, and outcome definitions extending beyond distance acuity are necessary before imaging-derived scores can independently guide consent, timing, or individualized follow-up.