A 59-year-old man had, over a period of 5 years, three different clinical scenarios which led to dynamic left ventricular outflow tract obstruction (LVOTO). Initially, this man who suffered from hypertrophic cardiomyopathy presented with asymmetric septal hypertrophy and systolic anterior motion (SAM) of the anterior mitral leaflet, along with mitral regurgitation. He was treated by septal myectomy and mitral valve repair with insertion of an artificial mitral ring. Several years later, he presented with severe LVOTO, this time related to the anteriorly displaced mitral coaptation site and the prosthetic ring. The ring and the anterior mitral leaflet were resected and a prosthetic mitral valve implanted. Several years later, the patient presented with LVOTO for a third time. It was now SAM of the remaining posterior leaflet that was responsible for the LVOTO.