Introduction: COVID-19 pandemia induced dramatic consequences worldwide bringing also enormous changes and trends in the field of education. Teachers and students were found quite unprepared with the arrival of the first COVID-19 wave, in March, April, May 2020 in Greece, as regards the immediate and obligatory implementation of distance learning through modern/advanced net technologies. Aim: To study and analyze statistically the assessment of secondary school students, on how they received distance learning, during the first outbreak of COVID-19 pandemia. Method: We conducted a quantitative research with a properly structured questionnaire which was filled in by 462 high school and senior high school students (both in general and vocational education sectors) after the school’s “reopening”. The proposed questionnaire was focused on three different groups of project questions. Following the reduction of factor variables by using factor analysis, the important parts were further looked into, with the help of the chi-square method. Results: 33.5% of the students were very satisfied with the distance learning. 18.2% of this group was interested in modern distance learning (P < 0.001), while only 12.3% of those considered asynchronous distance learning (exercises and material) (P < 0.001) as an interesting approach. In addition, 23.8% reported that teachers had difficulty in implementing distance learning (P < 0.001). 78.1% of the students were actually dissatisfied with the degree of their theoretical knowledge improvement (P < 0.001), while only 0.2% reported an improvement in laboratory lessons (P ≤ 0.05). A 13% of the students wished future implementation of distance learning. Of those, only 6.9% were satisfied with digital education (P < 0.001) and only 2.8% believed that conventional teaching can be enhanced in the future with distance learning (P < 0.001). Conclusions: The majority of students were not satisfied with the distance learning, believing that they had not received the degree of the expected benefit in terms of knowledge and skills. Therefore, distance learning seems, for the time, being not favored, by them, for its future implementation.