This study investigates prematurity’s impact on pediatric brains through radiology reports to explore prematurity’s relationship with severity of brain pathology, differences in frequent clinical indications for scan, and possible correlations between indications and pathological findings. Using a grading scheme created by neuroradiologists as well as a manual annotation software, we analyzed the severity of brain pathologies as well as annotated findings within the radiology reports. The results show that there are differences between severity of brain pathology per prematurity cohort, the most frequent clinical indications per cohort, and commonly noted findings for clinical indications. These findings align with other studies regarding prematurity’s role with severity of brain pathology and suggest correlations between top common findings and their disease characteristics based on the clinical indication. Further steps include detailing specific pathologies that determined report grades.