Athlete’s heart is typically accompanied by a remodelling of the cardiac chambers induced by exercise. However, although competitive athletes are commonly considered healthy, they can be affected by cardiac disorders characterised by an increase in left ventricular mass and wall thickness, such as hypertension. Unfortunately, training-induced increase in left ventricular mass, wall thickness, and atrial and ventricular dilatation observed in competitive athletes may mimic the pathological remodelling of pathological hypertrophy. As a consequence, distinguishing between athlete’s heart and hypertension can sometimes be challenging. The present review aimed to focus on the differential diagnosis between hypertensive heart disease and athlete’s heart, providing clinical information useful to distinguish between physiological and pathological remodelling.