Engaging students in self-reflection about their learning performance is a potentially promising pedagogical approach for supporting math learning. However, it is unclear how models for math learning in regular classrooms translate in a virtual environment. The purpose of this paper is to (a) analyze rich assessment data from virtual schools to explore the association between self-reflection and math performance, (b) compare the patterns found in student self-reflection across elementary, middle, and high school levels, and (c) examine whether providing opportunities for self-reflection had positive impact on student learning in a virtual learning environment. Implications for future research in this area are provided.