Achieving fluency in arithmetic operations is vital if students are to develop mathematical creativity and critical thinking abilities. Nevertheless, a substantial body of literature has demonstrated that students are struggling to develop such skills, due to the absence of appropriate instructional support or motivation. A proposed solution to tackle this problem is the rapid evolution and widespread integration of educational technology into the modern school system. To be precise, the Learning Management System (LMS) has been found to be particularly useful in the instructional process, especially where matters related to personalised and self-regulated learning are concerned. In the present work, we explored the aforementioned topics in the context of a longitudinal study in which 720 primary education students (4th–6th grade), from United Arab Emirates (UAE), utilised an LMS, at least once per week, for one school year (nine months). The findings revealed that the vast majority (97% of the 6th graders, 83% of the 4th graders, and 76% of the 5th graders) demonstrated a positive improvement in their arithmetic fluency development. Moreover, the Multiple Linear Regression analysis revealed that students need to practice deliberately for approximately 68 days (a minimum of 3 min a day) before seeing any substantial improvement in their performance. The study also made an additional contribution by demonstrating how design practice compliance with gamification and Learning Analytics in LMS may lead children to be fluent in simple arithmetic operations. For educators interested in LMS-based intervention, research implications and directions are presented