Digitalization through the use of Information and Communication Technologies is a phenomenon which has a great influence on our way of living. Organizations and society at large are not left behind. With the ubiquitous nature of technological devices, the need for digital competency in the constantly changing and advancing digital landscape is of utmost importance. In 2020, people’s lives and everyday activities were altered on a global scale, due to the outbreak of a viral disease named COVID-19, which resulted in a worldwide pandemic. Educators were suddenly faced with teaching challenges, due to the need for adoption of electronic learning tools and technologies for delivery of learning activities. Transitioning from traditional face-to-face teaching to distance learning was seamless for teachers who were digitally competent. However, the same transition for those with little or no digital competence and experience, resulted in great challenges in the delivery of academic activities through electronic learning platforms.The educational system however is still recuperating from the COVID-19 induced online method of teaching. The digital competence of teachers and their perceived experience during the transitioning phase has therefore become of great importance to study in qualitative research within an interpretive case study. As a result, this research work aims to compare responses of teachers who serve at two secondary schools in Greece and Sweden, both of which are located in the European Union. By answering two research questions, this study follows an inductive approach, using educational technology affordance framework. This provides insight into effective delivery of online learning in the education sector. The methodological approach of this research follows data collection through semi-structured interviews, addressed to teachers and validated through IT personnel who work in the selected schools; and the use of additional data collection through documents available online, which are related to the context of study. The data collected were examined using thematic analysis, followed by a general discussion, answers to research questions, and analysis about the theoretical framework. The findings of this research work reveal that there are interrelationships between teachers’ experience with online learning and their digital competencies, and these interrelationships play a major role in determining the successful implementation of digital technologies in academic activities. This is because, despite the challenges faced by teachers during the transitioning phase from traditional teaching method to online delivery, teachers with significantly higher levels of digital competence managed the new digital procedures easily. On the contrary, those with little or no digital competence level found the new procedure a difficult task. Thereby resulting in professional stress during this transition. Hence, the successful implementation of digital technologies into the educational work procedures is highly dependent on the digital skills levels of the teachers who will implement these technologies, as well as suitable and user-friendly platforms.This research work is descriptive, and it contributes to the knowledge as it concerns the need for digital competence among teachers. It provides further clarification on what school management, education specialists and software developers are doing with respect to improving the digital competence level of teachers. In addition to this, the study provides insights on what education policy makers can do to support teachers’ readiness towards digital skill acquisition. This is seen as a necessity to achieve optimum results for a successful future delivery of online education.