In the medical residency match process, applicants' ranking decisions are influenced by multiple factors related to training, geography, and lifestyle expectations. Ranking decisions directly impact match results, with implications for emotional outcomes such as happiness and stress. The present study explored the decision factors considered most important by applicants when creating rank order lists (ROLs), and how match outcomes and program factors predicted happiness, enthusiasm, stress, and life satisfaction. Senior medical students (n = 182) at a large public university in California completed surveys at three timepoints, spanning from shortly before Match Day to several months into PGY-1. Study findings support that both program-related (e.g., training quality, program size) and non-program-related (e.g., geography, work life balance) factors are important to applicants when making ROL decisions. Applicants who matched with their top choice program initially experienced emotional benefits, but these emotional differences did not persist into PGY-1, where all matched applicants had similar levels of emotion and life satisfaction. The emotional cost and benefits of matching with programs of different ROL positions (e.g., matching with top-choice program or not) were most apparent shortly after matching but in the long-term, a stronger predictor of PGY-1 emotions was perceived person-program alignment. Person-program alignment (e.g., call schedule, patient caseload) also predicted burnout in the first few months of a residency program. These findings show that, when applicants are making ranking decisions, they undervalue factors that predict stress and burnout during residency.