To our knowledge it is unknown whether concomitant inguinal lymph node dissection at the time of penectomy improves outcomes in patients with penile cancer. We analyzed predictors of regional recurrence as well as disease specific survival based on time of inguinal lymph node dissection. We also determined an optimal time to perform inguinal lymph node dissection. We reviewed the records of 84 consecutive patients with available nodal pathology findings. Recurrence-free and disease specific survival was estimated using the Kaplan-Meier method. Optimal time to inguinal lymph node dissection was assessed by ROC curves and used for dichotomization. Cox proportional HRs were used to identify predictors of regional recurrence after inguinal lymph node dissection. A total of 47 (56%) and 37 patients (44%) presented with cN0 and cN+ disease, respectively, during a median followup of 21 months. A cutoff point of 3 months to perform inguinal lymph node dissection was used to dichotomize the cohort into early vs delayed groups. Early dissection in 51 men demonstrated 5-year recurrence-free survival of 77% vs 37.8% in 33 who underwent delayed dissection. Positive node disease (HR 23.2, 95% CI 2.98-181.2) and early inguinal lymph node dissection (HR 0.48, 95% CI 0.21-0.98) were predictors of regional recurrence. Five-year disease specific survival was 64.1% and 39.5% in the early and late dissection groups, respectively. Three months appears to be an optimal window for performing inguinal lymph node dissection. While prospective trials are needed to define the role of upfront groin dissection, our results may help delineate patterns of referral and timing of inguinal lymph node dissection in patients with penile cancer.