The purposes of this study were to describe the learning outcomes of students with disabilities in senior high school, to establish a model to explain the effects of personal, family, and school experience factors on the learning outcomes of students with disabilities, and to determine the relationship between post-school and in-school outcomes. There were 496 participants selected in the 2011 and 2012 academic year from the database of Special Needs Education Longitudinal Study. The survey data obtained from questionnaires for teachers, parents, and students were used to conduct secondary analysis. Descriptive statistics such as frequencies and percentages, a PLS structural equation model, and multiple regression were used in this study. The results of this study were as follows: (1) Students with disabilities had the best learning performances in school, and most parents were satisfied with their students’ education in school; however, employment performance was the weakest upon leaving school. (2) School experience factors had the greatest influence on the school learning outcomes model, followed by student factors and family factors. (3) In-school outcomes effectively predicted postsecondary education, employment, social adaptation, and satisfaction after leaving school. In conclusion, the results of this study found that personal, family, and school factors have a significant impact on the learning outcomes of students with disabilities, and in-school outcomes can effectively predict postsecondary education, social adaptation, and satisfaction after leaving school.