This comparative study investigates politeness strategies used in Malaysian and Filipino student-teacher requesting emails. After analyzing a corpus of 40 student-teacher email requests that are written by Malaysian and Filipino university students, it is found that Malaysian university students use more direct (i.e., imperative, interrogative) requesting politeness strategies than their Filipino counterparts while Filipino university students use more indirect (i.e., positive, negative) requesting politeness strategies than their Malaysian counterparts. It is also revealed that Filipino students realize their requests longer with more strategies than Malaysian students as they produced more politeness moves than their Malaysian counterparts. This implies that while Filipino students tend to give more reasons and employ other strategies to justify their requests and appeal to their teachers, Malaysian students tend to directly, but politely using politeness mitigation markers, express the request. This study also shows that the use of negative politeness strategies is prominent among Malaysian and Filipino students; however, students also used positive politeness to establish solidarity with teachers with their offering of explanation and expression of goodwill. Although the findings of this study support the universality of request and politeness strategies, differences between the two groups of students are also proof of the culture-specificity of certain strategies. It is recommended to incorporate cross-cultural pragmatic awareness in language classrooms to encourage students to be more culturally adaptable as they engage in communication with people from different nationalities.