The sudden shift in the education system during the pandemic and its subsequent evolution during the post-pandemic era have been pivotal in fostering significant educational development and growth. However, this paradigm shift has not been without challenges. This paper aims to investigate the challenges faced by 68 mathematics teachers in four public elementary schools in the Philippines. The respondents were purposively selected to answer the study’s instrument. Using a descriptive survey research methodology, this study explored the five domains in teaching mathematics, namely planning lessons, executing lessons, assessment, mathematical knowledge, and using technology tools. This paper revealed that novice, experienced, and highly experienced teachers alike had moderate difficulty enriching mathematical knowledge and utilizing technology in teaching the subject matter. Moreover, teachers with more than five years’ experience had moderate difficulty in the five domains of teaching mathematics in the post-pandemic era. This finding emphasizes the widespread impact of the education shift for teachers of all levels of experience. The paper further emphasizes the importance of supporting experienced teachers during this transformative phase of formulating innovative learning activities and adapting to reimagined pedagogical concepts. Consequently, this study underscores the need for additional training interventions to enhance their mathematical knowledge and use of technology as an integral teaching tool.