Grade retention, the practice of holding a student back in the same grade, has been a controversial topic in the United States for decades. English learners, a growing population in US schools, are consistently identified for grade retention more often than their English-only counterparts. The purpose of this study is to test the impact of grade retention on a set of language learning outcomes (reading, listening, and writing) for English language learners over a seven-year period. The data was collected in a large urban school district in the south-central region that serves predominantly Spanish speaking natives. Retained students were matched with non-retained students for a quasi-experimental control group using Propensity Score Matching (PSM) techniques. Multilevel growth models, with time (level 1) nested within students (level 2), were applied to these two groups to estimate the effect of grade retention on their longitudinal trajectory for each language learning outcome. We found that after 7 years, matched-promoted students had higher levels of English proficiency than retained peers in all three domains: listening, reading, and writing.