Purpose: To characterize American Society of Ophthalmic Plastic and Reconstructive Surgery (ASOPRS) fellowship graduates’ career paths and contributions to society missions, including trends across gender, time, and geography. Methods: In this retrospective cohort study, ASOPRS fellowship graduates from 2000 to 2021 were stratified by demographics, time, and geography. Main outcomes were career paths and contributions to ASOPRS missions of advancing education, research, and quality of clinical practice. Results: Among 474 ASOPRS graduates, women increased from 19% (2000–2005) to 47% (2016–2021). Women contributed equally to men in most ASOPRS missions but were underrepresented as fellowship directors (p = 0.03). Over time, graduates after 2005 had higher publication rates (adjusted p < 0.001). Geographically, Northeast fellows (adjusted p = 0.034) and Midwest employment (adjusted p = 0.003) correlated with academic careers, while West employment conferred community careers (adjusted p < 0.001). Geographic retention near fellowship directly correlated with academic careers (adjusted p = 0.006), educational roles (adjusted p < 0.001), and publications (adjusted p = 0.006). Forty-one percent practiced in the 5 most saturated states, with fewer in the Midwest. The attrition rate of United States ASOPRS fellows who left the national workforce was 2%. Conclusions: From 2000 to 2021, ASOPRS fellows entered diverse career paths with increasing gender parity, though women were underrepresented as fellowship directors. Career paths and contributions to the field varied geographically. Graduates frequently practice in saturated states, potentially exacerbating access disparities in underserved regions. These findings highlight opportunities to address geographic differences, promote workforce diversity, and align fellowships with society objectives.