Focusing on learners’ active roles has brought Self-regulated Learning (SRL) to attention. Since its introduction in the mid-eighties, research has discussed several models and conceptual frameworks pertaining to SRL. Yet, more studies are required to explain how students achieve SRL and how it associates with academic achievement. Additionally, the potential of modern learning tools such as the Blackboard Learning Management System LMS and their role in promoting SRL are highly valued. To this end, the current study adopted a 27-item questionnaire based on different SRL models. It surveyed a sample of 165 students regarding their use of SRL strategies while they were engaged in online courses through Blackboard. The correlation between students’ use of such strategies and their academic achievement was ultimately calculated. It was found that students with higher academic performance apply a broader range of SRL strategies. Also, a variance can be seen in the type of strategies used. These findings are traced back to the features afforded by Blackboard, which result in SRL if they are appropriately deployed. Accordingly, teachers are called to utilise LMSs to promote SRL strategies and train their students in their use. These results are considered significant as most previous research has focused on the SRL concept rather than its effect on academic achievement. However, further empirical research on LMS features and their impact on developing SRL is recommended.