Principals have an important role to play in the implementation of digitalization in schools. They can be seen as role models for teachers with regard to information and communication technology (ICT) usage. Furthermore, there is nowadays a solid research linking educational leadership and management indirectly to student achievement. However, there is a lack of studies on the specific ICT usage of principals and the relationship with students' ICT skills. Against this background, our research aimed to find out whether different clusters of principals in Chile, Denmark, Germany, the Republic of Korea, and the United States can be identified on the basis of their leadership and management activities using ICT and whether there are differences in the distribution of the identified clusters across the countries. A latent class analysis was conducted using the International Computer and Information Literacy Study (ICILS) 2018 school questionnaire data. Across the five countries, three different clusters were identified based on principals' activities using ICT. Proportions of principals' distribution across the clusters varied significantly between the countries. In addition, it was investigated whether the clusters are related to students' computer and information literacy (CIL) using the means of student's scores in the computer based CIL test. No significant relation was found either when the five countries were considered together or individually.