Background: Mentors often provide advice to students regarding selection of Advanced Pharmacy Practice Experience (APPE) rotations to strengthen their candidacy for a residency position. However, the impact of APPE characteristics on the chances of matching is unknown. Objective: To determine the impact of APPE characteristics on Post Graduate Year-1 (PGY1) residency match rates at a Midwest US college of pharmacy. Methods: Graduates from a single college of pharmacy who participated in the PGY1 match in 2015 or 2016 were included. Match data were obtained from National Matching Services. APPE characteristics (e.g., rotation timing relative to the Midyear Clinical Meeting [MCM], rotation type, and setting) were stratified by matched status. Independent predictors were identified using multivariate logistic regression and tree-based models. Results: Ninety-nine students were included with 57 matching (57.6%). Students completing an infectious diseases rotation (75 vs. 51%; p = 0.028), a hospital rotation before the MCM (67 vs. 47%; p = 0.039), or a rotation in an ambulatory care clinic (67 vs. 47%; p = 0.045) were more likely to match. Students completing an independent community pharmacy rotation were less likely to match (8.3 vs. 64%; p < 0.001). After multivariate adjustment, all of these factors were associated with the likelihood of matching except completion of an infectious diseases ( p = 0.077) or ambulatory care rotation ( p = 0.073). Conclusion: A hospital rotation prior to the MCM was positively associated with matching while completion of an independent community pharmacy rotation was associated with non-matched status. The utility of these findings in guiding APPE selections for students pursing residency should be explored.