This study investigated the impact of Head Start, disability status, and receipt of an Individualized Education Program (IEP) on early language, literacy, and mathematics skills for low-income children with language, cognitive, emotional/behavioral, sensory, and physical disabilities. Secondary analysis of data was performed on a sample of children with disabilities (N = 570) drawn from the Head Start Impact Study, a nationally representative study of approximately 5,000 children randomly assigned to Head Start or non-Head Start programs. Results of ordinary least squares regression analyses indicated that Head Start participation enhanced outcomes for children with multiple disabilities; language, literacy, and mathematics skills at age 5-6 years were higher for these children compared to non-Head Start attendees. Head Start children with disabilities were more likely to have an IEP, though IEP receipt was associated with lower language, literacy, and mathematics scores among all children. There is a need to ensure that Head Start, and programs similar to Head Start, are more widely available to provide comprehensive, quality early childhood programming to children with cumulative risk factors (low income, multiple disabilities). Future research should clarify why IEP receipt was associated with poorer cognitive outcomes. (author abstract)