In current era of net-centric computing, the availability of a web-based leave management system has become an essential and indispensable tool for any organization and corporation. It can track and manage a variety of employee leaves, as well as process requests for time off for employees. However, there were issues raised concerning inefficiency, downtime, and delays in the processing and approval of leave requests in the human resources departments of corporations and agencies. This paper explains why it is necessary to develop a system that uses web-technologies to eliminate bottlenecks in getting leave approved on time. This paper used a qualitative research approach to gather insights and familiarity with what is in existence so that more research can be done. Data was gathered through interviews, scenario generation using stakeholders' and participants' experiential narratives, and analysis of present processes and structures. The development approach followed a software development methodology. A web-based leave management system (WBLMS) was designed using Unified Modelling Language (UML) tools with its database designed using SQLite, implemented using web technologies such as HTML, CSS, Python Programming language and its Django framework and evaluated using DeLeon and McLean Information theory. The outcome of the system evaluation revealed a positive result. Upon the use of the system developed, the response from respondents yielded 76.67% satisfaction rate. This is indicative of the fact that when users (junior and senior staff) use the leave system, it was considered acceptable and good enough to achieve or meet the requirement specified). The system also yielded 81.67% accuracy and gave 81.67% ease of use. The paper concluded that a proposed leave system developed enhance user satisfaction, increase productivity and ensure efficiency as well as the effectiveness of the process and employees while reducing the time taken in processing leave application.