Purpose: School-age children with unilateral hearing loss are at an increased risk of exhibiting academic difficulties. Yet, approximately half of children with unilateral hearing loss will not require additional support. There is a dearth of information to assist in determining which of these children will express academic deficits and which will not. The purpose of this study was to identify hearing- and health-related factors that contribute to adverse educational progress in children with permanent unilateral hearing loss. Specific indicators of academic concern identified during school age included the need for specialized academic services, receipt of speech-language therapy, or parent/teacher concerns for academics or speech-language development. Method: This study provides an in-depth analysis of a previously described patient cohort developed from de-identified electronic health records. Factors of interest included potentially relevant hearing-related risk factors (e.g., degree, type, and laterality of hearing loss), in addition to health-related factors that could be extracted from the electronic health records (e.g., sex, premature birth, history of significant otitis media). Results: Being born preterm, having a history of pressure equalization tubes or having conductive or mixed hearing loss more than doubled the risk of demonstrating adverse educational progress. Laterality and degree of loss were generally not significantly related to academic progress. Conclusions: Approximately half of school-age children with permanent unilateral hearing loss in this cohort experienced some academic challenges. Birth history and middle ear pathology were important predictors of adverse educational progress.