(1) Objective: To determine the incidence, visual outcomes and risk factors associated with the recurrence of primary retinal detachment (RD) in a tertiary hospital. (2) Methods: A retrospective observational study was conducted, and data were collected on all eyes diagnosed with primary RD between January 2017 and December 2020. A detailed database was generated with data on anatomic and visual outcomes, and surgical technique information, for all the cases. (3) Results: 570 eyes with primary RD were included. Mean annual incidence of primary RD was 21.8 cases per 100,000 inhabitants. Mean follow-up time was 465 (±410.5) days. Mean time to redetachment was 114.4 (±215.8) days, with the median being 35 days. Statistically significant variables related to a higher risk of recurrence were: male sex (p = 0.04), type of tamponade (p = 0.01), surgeon (p = 0.035), inferonasal (p = 0.002) and inferotemporal (p = 0.032) involvement, complex RD (p < 0.001) and ocular comorbidity (p < 0.001). More satisfactory final visual acuity (VA) in patients not suffering redetachment was associated with shorter duration of central vision loss. (4) Conclusions: Sex, type of tamponade, inferior detachment, RD complexity, surgeon and ocular comorbidity were identified as prognostic factors for recurrence. Worse final postoperative VA was found in patients referring central vision loss for more than 4 days before surgery.