IMPORTANCE Communication between applicants, mentors, and training programs is common before the residency and fellowship match. Few studies have examined the association of prematch communication on final match outcomes. OBJECTIVES To report various characteristics of the vitreoretinal surgery fellowship match and to examine the association of mentor-to-program communication and applicant disclosure of their number 1 ranking with the probability of matching number 1. DESIGN, SETTING, AND PARTICIPANTS In this cross-sectional study of the 2016 and 2017 vitreoretinal surgery fellowship matches, an online survey examined (1) number of applications submitted, (2) number of programs ranked, (3) rank order of final match, (4) total application and interview-related costs, (5) mentor-to-program contact, (6) applicant disclosure of number 1 ranking, and (7) mentor disclosure of number 1 ranking. A link to an anonymous online survey was sent to 198 matched fellows (105 fellows from the 2016 match and 93 from the 2017 match). MAIN OUTCOMES AND MEASURES Survey responses regarding the vitreoretinal surgery fellowship application process. RESULTS The survey was sent to 198 matched fellowship applicants, and 152 (77%) completed the survey. Of the 105 matched applicants in 2016, 21 (20%) were women. Of the 93 matched applicants in 2017, 24 (26%) were women. Matched applicants applied to a mean (SD) of 34 (17) programs (range, 1-85) and ranked a mean (SD) of 12 (4) programs (range, 1-27). Of 152 applicants, 66 (43%) matched at their number 1 ranked program, 23 (15%) matched number 2, and 21 (14%) matched number 3. The mean (SD) total cost was $5500