Currently, an increasing cultural diversity in Latin American countries is affecting different dimensions of society, Music Education being one of them. In Chile, the rise of immigration, especially of people from Caribbean countries, has added to the continuing historical sociocultural issues of indigenous people and maps wider shifts in the cultural diversity of the country. However, there is a lack of research in Chilean Music Education related to cultural diversity, especially in terms of teachers’ pedagogical practices. In this sense, the research seeks to address this gap, comprehending in depth the pedagogical practices of two Chilean music teachers and contributing to the teachers’ reflection on their own pedagogical practices. By means of a “Life history research” methodology (Goodson & Sikes, 2001), developed by extended interviews, the teachers’ influences, challenges, approaches and values are depicted in relation to the issue of cultural diversity in Chilean Music Education. The findings suggest that those teachers who participate in this research acknowledge and demonstrate a strong consideration of the cultural diversity embodied by their students and work with the intention to be culturally broad in their music teaching. However, teachers’ pedagogical approaches are content dominant, looking for what rather than the how, with a tendency to fix a certain cultural music tradition as a static entity. Nevertheless, this issue is predominantly influenced by teachers’ previous education and an on going engagement with their own professional development. Generalizations from these findings are not claimed. However, it is possible to further consider the relevance of teacher’s conditions and education, as well as the balance of content and pedagogical approach.