Accurate assessment and evaluation of medical curricula has long been a goal of medical educators. Current methods rely on manually-entered keywords and trainee-recorded logs of case exposure. In this study, we used natural language processing to compare the clinical content coverage in a four-year medical curriculum to the electronic medical record notes written by clinical trainees. The content coverage was compared for each of 25 agreed-upon core clinical problems (CCPs) and seven categories of infectious diseases. Most CCPs were covered in both corpora. Lecture curricula more frequently represented rare curricula, and several areas of low content coverage were identified, primarily related to outpatient complaints. Such methods may prove useful for future curriculum evaluations and revisions.