Understanding mathematical concepts involve developing an intuitive grasp of the underlying ideas and principles that govern mathematical operations and relationships. The primary purpose of this study is to investigate the difficulties and coping strategies in understanding mathematical concepts. This study used an explanatory sequential research design through the collection and analysis of quantitative data followed by a qualitative inquiry. To collect data, the researchers developed questionnaires for the quantitative and qualitative inquiries, which were validated by external experts. The sample of the study for the quantitative part included conveniently selected 297 students from a private Higher Education Institution (HEI) in Tagum City, Davao del Norte, Philippines, in the academic year 2017-2018. In addition, seven (7) individuals participated in the Key Informant Interviews (KIIs). One session of Focus Group Discussion (FGD) was also organized with seven first-year students enrolled during the second semester of S.Y. 2017-2018. Five skills areas were examined: number fact, arithmetic, language, informational, and visual. Based on the results, students find difficulties in understanding mathematical concepts, specifically in visualizing mathematical concepts and manipulating geometrical shapes and spaces meaningfully. The students also demonstrated difficulties in analyzing the problem, understanding the concept, identifying the correct solution, establishing the equation, and simplifying the expression. In addition, the students cope with the difficulties through self-perseverance, expert consultation, reading and studying, constant practice, and confidence building. Mathematics teachers are recommended to design need-based teaching strategies to optimize student learning.