The objective was to evaluate the growth in pharmacy student performance in entrustable professional activity (EPA) assessments across the experiential curriculum based on preceptor assessments on an entrustment–supervision (ES) scale. This retrospective cohort study used assessments based on the 2016 American Association of Colleges of Pharmacy Core EPAs and an expanded ES scale during introductory and advanced pharmacy practice experiences (IPPEs/APPEs) in the third and fourth professional years from fall 2020 to fall 2023. The primary outcome was the change in ES level, assessed by preceptors over time. The secondary outcomes were growth rates across types of experiences, training environments, and experience order. A conditional growth curve model and ordinal mixed effects model were used to demonstrate discrete entrustment decisions. A total of 509 students received 12,426 assessments by 557 preceptors. Raw ES levels and unconditional growth curves for EPA show increases in entrustability from years P3 to P4. Comparing care settings, there was lower entrustment in inpatient than outpatient settings and at academic medical centers than other settings. There were no significant differences in ES levels regardless of which IPPE was taken first. However, when the first APPE was an inpatient medicine experience, ES levels across APPEs for EPA 3 were higher when compared to ambulatory care as the first APPE, and they were higher for EPA 5 when compared to community pharmacy as the first APPE. Paired with ES scales, EPAs can be integrated into pharmacy experiential curricula to demonstrate longitudinal growth in student entrustment.