Closed proximal muscle rupture of the biceps brachii is a rare injury. In this report, two cases of closed proximal muscle rupture of the biceps brachii after wakeboard traumas are described. Both patients presented with a swollen arm, weakness during flexion, and a mass in the affected forearm. Magnetic resonance imaging showed displacement of the biceps brachii into the forearm. The rupture was successfully treated with muscle removal in one case and muscle repair in the other. In patients with a wakeboard trauma and similar presentations, closed proximal muscle rupture of the biceps brachii should be suspected.