BackgroundHouse staff participating in surgical residency programs are often comprised of adult learners from the millennial generation (Gen Y). With the increasing gap in both age and learning styles between these residents and their educators, their educators are struggling to keep them academically engaged. PurposeThe purpose of this study was to measure the association between implementing a digital online Jeopardy!® (Sony Pictures Studios, Culver City, CA) style game (digital game) (Factile© Solace Creative, LLC, Melbourne Beach, FL) into oral maxillofacial surgery (OMS) resident didactic training and Oral and Maxillofacial Surgery In-service Training Examination (OMSITE) scores. Study Design, Setting, SampleThis study was a retrospective cohort study conducted at The New York Presbyterian Hospital/Weill Cornell Medicine (NYP/WCM). OMS residents who took the OMSITE exam were included in the study. Exclusion criteria included OMS residents who did not take the OMSITE in a given year. Independent VariableThe independent variable was the timing of the implementation of the digital game, divided into before and after implementation. Main Outcome VariablesThe primary outcome variable was OMSITE scores. CovariatesCovariates included demographics (age, gender, race), year of training, and number of examination attempts. AnalysesDescriptive and bivariate statistics included Fisher's exact test and Wilcoxon rank sum test. Linear mixed modeling was performed to take into account multiple observations per participants. ResultsThe sample composed of 14 resident subjects with a median age of 27.5 [27.0, 28.7]. Females represented 29% of the cohort. Seventy-one percent of the participants were PGY-1. The median (interquartile range [IQR]) OMSITE score pre-implementation: 61 (48,71) and post-implementation: 79 (68,87). On average, the OMSITE scores, improved significantly following the implementation of this study modality (p < 0.001). ConclusionsDigital games may be an effective learning tool to prepare residents for OMSITE by promoting academic engagement.