Background/Objectives: Pneumothorax can be a major complication of neonatal lung diseases. We aim to delineate trends and describe the main outcomes related to pneumothorax in very preterm infants (VPI). Methods: Preterm infants p p = 0.309). Patients with pneumothorax exhibited higher rates of severe intraventricular hemorrhage (IVH) (Odds Ratio (OR) = 2.0 (95%CI 1.3–3.1), p = 0.003), bronchopulmonary dysplasia (OR = 2.7 (95%CI 1.7–4.4), p p p p < 0.001), we found no significant difference in pneumothorax-related deaths. Conclusion: Pneumothorax remains a serious threat to VPI, leading to a higher incidence of morbidity, and mortality attributable to this complication has not decreased. Preventive strategies and early recognition are essential for improving disability-free survival in VPI.