Following the contemporary indefinite prevalence of lesson preparation practices among teachers, this study explored the philosophy behind teachers' lesson preparation practices in view of enhancing effective teaching and learning in Uganda. While the study’s teachers' lesson preparation practices were conceptualized as making schemes of work and lesson plans, the philosophy underlying these practices were conceptualized as teachers’ beliefs about students' learning, the nature and sources of valuable knowledge, and the values they aim to instill in students. The Danielson’s 1996 framework for effective teaching model informed this qualitative descriptive triad case study, underpinned by the interpritivist paradigm. Nine teachers from three schools (three from each school) in Kayunga district, participated in this study. Data was collected from the teachers, their head teachers, directors of studies and students. The findings revealed that philosophy underlying teachers’ lesson preparation practices is pragmatism reflected in learning through doing, valuing experience and reflection, adapting education to real-world contexts, and fostering habits of mind that prepare students for active participation in society. The study recommends that school managers such as head teachers should regularly follow up closely on teachers’ pragmatic lesson preparation practices, putting into consideration that drawing formal lesson plans may not be the only effective way of planning to teach.