Introduction Little is known about gender’s role in chronic venous insufficiency (CVI). The aim of this study was to evaluate the impact of gender on outcomes of iliac vein stenting(IVS) for CVI. Methods 866 patients who underwent vein stenting for CVI at one institution from August 2011 to June 2021 were analyzed via retrospective review. Patients were followed up to 5 years after initial stent placement. Presenting symptoms were quantified using Venous Clinical Severity Score(VCSS), Clinical Assessment Score(CAS), and Clinical, Etiology, Anatomy, and Pathophysiology (CEAP) class. Reoperations after initial IVS were recorded. Major reoperations were defined as iliac interventions using venography. Minor reoperations were defined as thermal ablation. Multivariate logistic regression models were used determine odds of any and major reintervention. Results Compared to females, males pre-operatively presented with a higher mean CEAP class (3.6 vs .3.3; P < .001), VCSS composite (11.3 vs .9.9; P < .001), and smoking history (134 vs .49; P < .001). The 2 groups were similar in age ( P = .125), BMI( P = .898), previous DVT ( P = .085), diabetes ( P = .386), hypertension ( P = 1.0), and CAD ( P = .499). Multivariate analyses revealed no association between gender and any reintervention (OR, 1.02; 95%CI, .71-1.46; P = .935) or gender and major reintervention (OR, 1.39; 95% CI, .86-2.23 P = .177). There were no differences in number of stents placed ( P = .736) or symptomatic improvement at 1 month ( P = .951), 3 months ( P = .233), 6 months( P = .068), and greater than 1 year ( P = .287). At the 1 year follow-up, the male cohort had higher CAS values than females P = .034). Males had larger reduction in composite VCSS than women at 1 year (5.1 vs. 3.8; P = .003) and 3 years (5.3 vs .3.7; P = .031) of follow-up and similar levels of improvement in post-op (4.0 vs .3.5; P = .059), 2 years (4.3 vs .3.8; P = .295), 4-years (5.1 vs .4.6; P = .529), 5 years (5.6 vs .4.2; P = .174), and 6 years (5.93vs.3.3 P = .089). Conclusions In a single site study of IVS in patients with CVI, males tended to present worse symptoms than females. After surgery, however, both cohorts showed improvement, and both seemed to improve to the same degree of residual symptoms.