This study leverages naturally occurring lotteries for oversubscribed Boston Public Schools prekindergarten program sites between 2007 and 2011, for 3,182 children (M = 4.5 years old) to estimate the impacts of winning a first choice lottery and enrolling in Boston prekindergarten versus losing a first choice lottery and not enrolling on children's enrollment and persistence in district schools, grade retention, special education placement, and third-grade test scores. There are large effects on enrollment and persistence, but no effects on other examined outcomes for this subsample. Importantly, children who competed for oversubscribed seats were not representative of all appliers and almost all control-group children attended center-based preschool. Findings contribute to the larger evidence base and raise important considerations for future prekindergarten lottery-based studies. [This is the online version of an article published in "Child Development" (ISSN 0009-3920).]