Purpose: To assess the most important variables that influence an applicant’s selection of a vitreoretinal training program. Methods: This single-center study, spanning from 1966 to 2025, included 100 vitreoretinal surgery fellows at the University of Iowa. A survey was sent to former fellows that included demographic questions regarding decade of fellowship completion, age, geographic region of residency training, sex, and practice setting. Respondents were asked to rank the importance of a series of variables when selecting their training program. Results: Although limited by the response rate (30%), respondents’ most important variables when selecting a program were quality of surgical and medical retina training, exposure to multiple surgical techniques and subspecialties, and institutional reputation. The least important variables were presence of an injection clinic, presence of a surgical simulator, presence of a Veterans Affairs hospital, nearby parking, and salary. Trends were found between practice setting and work-life balance, location, institutional reputation, and quality of surgical training. There was no statistically significant relationship between age, sex, location of residency training, and any of the variables analyzed. Conclusions: Quality of surgical and medical retina training was the most important variable to fellows matching at our center. An applicant’s desired future practice setting may be among the most important criteria when selecting a training program and should be considered in both the mentoring and matching processes.