Grade retention is a commonly used intervention for children who struggle in school. However, empirical research does not unequivocally support its efficacy. Of particular interest are the prevalence, predictors, and outcomes of students who are retained more than once in elementary school. To date, limited research examines students who are held back multiple times in school. We examined multiple retentions within a large, ethnically diverse (52.7% Latinx, 43.7% African American/Black, 3.6% White/Asian/Other) sample of students who had been retained at least once (N = 5,490). Most of these students (90.3%) were receiving free/reduced-price lunch. This sample of retained students was derived from a larger dataset (N = 32,551; 58.3% Latinx, 34.5% African American/Black, 7.2% White/Asian/Other). Results indicate that twice-retention was rare in this sample, with only 460 (1% of all students; 8% of students who were retained) being held back more than once. When twice-retention did occur, the second retention happened most often in 3rd grade, likely due to the state-wide promotional gate. In this sample, students who were retained twice performed more poorly early on in school and were much more likely to be Black and receive free lunch. Students who were retained twice had poorer outcomes on 5th grade GPA, even after controlling for poverty and initial school performance with small effect sizes. Students who were retained twice performed more poorly on 5th grade standardized reading with a small effect size, but no differently on math tests. These results suggest that, within this predominantly low-income, ethnically diverse sample, multiple retentions in elementary school does not appear to benefit struggling students, and this practice disproportionately affects Black children. These findings suggest retention policies should be more closely examined.