We tested the hypothesis that phosphodiesterase type 5 inhibitor (PDE5i) use would be associated with increased likelihood of condom breakage using an event-specific analysis. A convenience sample of 440 men completed an internet-based questionnaire that assessed variables pertaining to the last time they used condoms for penile-vaginal intercourse (PVI). A bivariate (screening) analysis was performed to identify covariates for a multivariate analysis using logistic regression. Altogether, 5.9% of the men reported breakage and 9.5% reported PDE5i use during the last time a condom was used for PVI. Among men who had used PDE5i during the last condom-protected occasion of PVI, 11.9% reported breakage compared with 5.3% of those not reporting PDE5i use. Adjusting for men's age, ethnic minority status, marital status, reported duration of PVI and alcohol use at last PVI, those using PDE5i were about four times more likely to also report condom breakage (AOR 4.02; 95% CI 1.20 to 13.48; p = 0.04). Of note, duration of PVI was independently associated with breakage (AOR 1.36; CI 1.02 to 1.83; p = 0.04). Findings suggest that PDE5i use may potentially be associated with increased odds of condom breakage among some men.