This study explained the pedagogical dilemmas of handling non-specialized subjects from the perspective of English teachers in private and public schools. It examines how the challenges significantly impact students' academic performance. A total of ten (10) participants are considered in this study who joined the in-depth interview and focused group discussion, respectively. Five of them participated in the in-depth interview (IDI) while the remaining participants attended the focus group discussion (FGD). Phenomenological research is the main basis for gathering all information in this study since it involves understanding the universal experience through interviews with subjects and examining their views about their experience. The result highlighted the challenges and opportunities in teaching subjects beyond specialization, emphasizing the role of educators' expertise in promoting effective and quality education. The result revealed that while the phenomenon is evident and significantly improves educators’ competencies in cross-disciplinary teaching, several challenges hinder its effectiveness. It also discusses how school administrators can play a pivotal role in providing professional development for teachers to acquire the subject competencies based on the curriculum and support student success in non-specialized subjects. These limitations create operational difficulties, affecting school performance, teachers’ pedagogical approaches, and students' learning experiences. The study highlights the implications of these findings for educational institutions, school administrators, and stakeholders.