Handlebar injury is an uncommon mechanism of blunt injury with a recognised risk of injury to groin vasculature. We describe two cases involving bicycle handlebar injury to the groin and their different respective outcomes. Patient A sustained a significant limb-threatening injury following significant arterial and venous disruption. Surgical intervention was able to restore arterial flow via interpositional vein graft, while venous injuries were ligated. As a result, the patient was discharged with a viable limb and a non-disabling swelling from venous pathology. Patient B, of identical age, also sustained a bicycle handlebar injury to the groin but without the need for surgical intervention. Active observation and the use of repeat imaging suggested spontaneous cessation of any minor arterial bleeding; the patient made a rapid recovery and was discharged soon thereafter. These cases highlight the variability in outcome stemming from this injury mechanism and that early recognition is vital for limb viability.