This study examines students' transition from grade X to CAIE A-level in the context of school mathematics curriculum in Nepal. This study is based on the qualitative study design covering a total of ten participants from two A-level schools in Nepal. Content analysis and phenomenology were used as methodological approaches to the study. The study finds that there exist challenges for the students of Nepal during the transition process in different dimensions. The study concludes that there is a substantial gap in contents and assessment systems between the two mathematics curriculums. The study recommends the bridging of mathematical contents, preparing and implementing transition strategies in schools where students transit from grade X to CAIE A-level.