This study uses data from the Early Childhood Longitudinal Study, 2010-2011 to better understand the rates of grade retention during elementary school and the factors associated with this grade retention. Using matched student-teacher and student-principal data, I examine the student-, teacher-, and school-level factors associated with a student's probability of being retained. I then apply within-student comparisons to examine the extent to which students with a teacher or principal of the same race/ethnicity had a lower probability of being retained. No evidence of a relationship is found between student-teacher and student-principal racial/ethnic matching and reduced grade retention for Black, Latinx, or White students.