Background: Orbital floor fractures are among the most common maxillofacial injuries and represent the predominant type of isolated orbital fractures. Residual diplopia is a common complication in these patients, and its management is quite challenging. The present study aimed to investigate predisposing factors for late residual diplopia following surgical repair of orbital floor fractures. Methods: Patients presenting with maxillofacial trauma between 2019 and 2024 were retrospectively analyzed. Individuals diagnosed with orbital floor fractures were included. Data regarding concomitant wall involvement, preoperative diplopia, mechanism of trauma, time interval between trauma and surgery, defect size, and postoperative enophthalmos were obtained from patient records. Patients with a follow-up period of less than 3 months were excluded from the study. These variables were statistically compared to assess their relationship with persistent postoperative diplopia. Results: A total of 109 patients with orbital floor fractures were evaluated. Post-traumatic diplopia was observed in 15.6% of cases. The presence of residual enophthalmos was significantly associated with residual diplopia (p< 0.001): 56.3% of patients with enophthalmos exhibited diplopia compared to 8.6% without. “Floor+rim” fractures demonstrated a higher incidence of diplopia (20.9%) than other wall combinations (p= 0.054). The interval between trauma and surgery was not correlated with diplopia (p= 0.425), whereas increasing defect size was significantly associated (p= 0.039). Although diplopia was more frequent in assault (19.4%) and collision (28.6%) cases, the difference was not statistically significant (p= 0.578). Conclusion Persistent postoperative diplopia remains a challenging complication after orbital fracture repair. The strong association between residual enophthalmos and diplopia underscores the need for meticulous intraoperative reconstruction and close postoperative follow-up to optimize functional and aesthetic outcomes.