Objectives: The main aim of this study was to investigate the factors that influence students’, academicians’, clients’, as well as developer’s preferences in choosing their preferred approach in system development, namely structured analysis design (SAD) or object-oriented analysis and design (OOAD). Methods: The research design was based on a survey methodology and a case study. For the survey, questionnaires were administered to 30 students and 38 academicians, who were randomly selected from several Malaysian universities. For the case study, the requirements of the information system were modeled and presented to several clients to elicit their feedback. The survey data were analyzed using SPSS Findings: The result shows that students preferred the use of OOAD approach, which clearly outnumbered those who preferred the SAD approach, which stood at 33%. Interestingly, the majority (53%) of academicians preferred the use of a mixture of both approaches. Likewise, the clients shared a similar view with the academicians, whereas the developer preferred the OOAD approach. Application/Improvements: Clearly, the findings suggest that both approaches are essential, but the one that is widely used by developers and preferred by students is OOAD, and thus should be given priority when it comes to structured analysis and design. As such, curriculum designers and institutions of higher learning, particularly those offering system analysis and design and related courses, should make the necessary changes to the existing curriculum such that the academic programs offered will be able to produce highly competent and skilled analysts and designers as required by the industry.