Objectives: The use of online social networks (OSNs) such as Facebook and Twitter has proliferated, and besides the numerous positive outcomes associated with such, there is a rising number of individuals experiencing the negative consequences resulting from an excessive use of OSNs. Obsessive-compulsive disorder (OCD) has been associated with compulsive social media use, which can significantly trigger social media fatigue. In terms of outcomes, there is a need for research on the role that social media fatigue plays in the educational context. The present study explores compulsive media use as a mediator between OCD tendencies and social media fatigue, and social media fatigue’s effect on educational outcomes, to render a deeper understanding of the internet-related behaviours of those who exhibit OCD tendencies. Method: Three hundred and thirty-nine students (Mage = 22.29, SD = 5.64) completed a cross-sectional online survey including the Obsessive-Compulsive Inventory–Revised (OCI-R) scale, the Bergen Social Networking Addiction Scale (BSNAS), and measures related to social media fatigue, and academic motivation, effort and achievement. Results: A simple mediation analysis revealed that OCD is both directly and indirectly (through compulsive media use) related to social media fatigue. OCD appears to significantly predict social media fatigue and compulsive media use, which in turn significantly predicts social media fatigue. Simple linear regression analyses between social media fatigue and academic motivation and effort, and GPA, showed that social media fatigue did not significantly predict academic motivation or effort, but did significantly predict GPA score. Conclusion: Individuals with higher levels of OCD symptoms are more likely to directly experience social media fatigue, or indirectly experience it through compulsive media use. Social media fatigue can positively influence academic achievement. Practical implications and directions for future research are discussed.