The workloads and well-being of the teachers are important factors to consider when working towards achieving our educational goals. In this study, we investigated the teachers’ workloads and well-being and explored their relationships with the academic performance of the students. High school teachers from three divisions in Northern Mindanao, Philippines participated in a survey on the extent of their workloads and their workplace well-being. Majority of the respondents reported moderate to heavy workloads. They also responded positively in all three domains of well-being considered in this study. Comparing the teachers’ responses with the National Achievement Test (NAT) scores of their students reveals no significant relationships. The results suggest that there is no direct link between the teachers’ workloads and well-being and their students’ academic performance. However, the moderate to heavy workloads reported by the respondents reverberate a pressing issue in the educational workforce. Furthermore, based on the responses, among the three domains of well-being, the environmental domain scores the lowest. Thus, for policymakers and school administrators, we recommend considering the work environment and the workloads of the teachers in adopting policies and measures relevant to the teacher working conditions in order to address the issues related to them.