Confidence-Based Learning or CBL is a methodology used for both learning and training that measures a learner's knowledge level and quality prior to any knowledge dissemination. Measurement of knowledge is done by determining both the correctness and confidence that the learner has. CBL works on the basis of three different phases that a learner has to pass through: (i) Diagnosis - the system determines the exact knowledge a learner has prior to learning or training. (ii) Prescribe - once the knowledge gaps and shortcomings are identified, the CBL offers a customized learning plan that will fill up the gaps and increase the confidence of the learner. (iii) Learn - in this phase the learner start learning according to the customized plan. In present day scenario a number of LMS are available in the market that had been designed and developed for conventional web based teaching - learning system, and hence cannot be directly used for CBL. On the other hand, web based CBL being a new area of research, no such significant efforts have been recorded for developing a general purpose LMS. In this research work, UML based design technique has been applied to express the design requirements and several diagrams like use-case diagrams, activity diagrams, etc have been drawn for the purpose. Multiple choice questions with confidence factor have been utilized for measurement. Goals of the proposed LMS include identification of learners' lack of knowledge, identification of necessary learning objects to supplement the gaps, providing opportunity to the learner to acquire the knowledge through web based system, reassess the candidates, etc. For this purpose a detailed requirement analysis has been done and business rules have also been formed.