Information technology is a widely used tool to facilitate teaching and learning activities in tertiary education. Distance learning courses designed and delivered via information technologies present opportunities to students with difficulties in enrolling and attending courses in higher education. Students enrolled in these courses are expected to participate in the technology supported learning environments and interact with the content presented through distance education technologies. This study is designed to elaborate on the factors that have effect on student success in two undergraduate courses taught through distance education technologies. Participants of this study are 124 freshman students. The aim of this study is to investigate the effects of student-content interaction on academic performance via a detailed analysis of data retrieved from the distance learning environment. This study will also shed light on the relationship between gender differences and success levels in distance education courses with respect to participation performance.