Diastolic dysfunction is primarily an echocardiographic diagnosis. Its clinical counterpart is diastolic heart failure, where the heart has difficulty to fill at normal pressure and the patient develops signs of pulmonary edema. Although diastolic dysfunction is common in adults, limited information is available in preterm infants. The aim of this study is to explore left ventricular diastolic dysfunction and diastolic heart failure in preterm infants and describe clinical manifestations in this population. This is a retrospective observational study in preterm infants < 30 weeks’ gestation who received an echocardiography in the first 4 weeks after birth. Diastolic dysfunction was graded using a population-specific adapted version of the adult recommendations for the evaluation of left ventricular diastolic function by echocardiography. Left ventricular diastolic dysfunction was absent, indeterminate, and definite in 82%, 14%, and 4% of the 168 echocardiograms analyzed, and is associated with increased respiratory signs and respiratory deterioration at 48 h before echocardiogram. In seven infants, diastolic heart failure was diagnosed with both ultrasound and clinical signs. The cumulative risk of diastolic dysfunction increased with the increasing postnatal age and a patent ductus arteriosus. Evidence of left ventricular diastolic dysfunction on echocardiography is relatively common in preterm infants, while the left ventricular diastolic heart failure is less frequent. Prolonged exposure to volume load was the most common cause.