Background: Previously, researchers investigated the career accomplishments of USU medical graduates using the data from a USU alumni survey. To better understand if such accomplishments are related to military retention, the current study investigates the relationship between accomplishments (such as military career milestones and academic achievement) and military retention. Methods: Utilizing the responses to the alumni survey sent to USU graduates in the Classes of 1980 to 2017, the researchers investigated the relationship between a series of survey items (e.g., military rank, medical specialties, and operation experiences) and military retention. Results: Among the respondents who had a deployment history in support of an operational mission, 206 (67.1%) stayed longer than their initial active duty service or planned on staying longer than their current active duty service commitment. Fellowship directors (n = 65, 72.3%) showed a higher retention rate than other positions. The PHS alumni had the highest retention rate (n = 39, 69%) of the military branches, whereas physicians in medical specialties with higher demand (e.g., otolaryngology and psychiatry) showed less promising retention. Conclusions: By conducting future research on underlying reasons as to why full-time clinicians, junior physicians, and physicians in medical specialties with higher demand showed less promising retention, stakeholders will be able to identify what needs to be addressed to retain highly skilled physicians in the military.