Studies on the determinants of school results have shown that they depend largely on the context of learning. Concerning the pandemic, teachers have been forced to find online teaching methods, which leads us to the central issue of this study of whether the effectiveness of online education depends on teachers’ digital skills. Therefore, in this study, we analyzed the perceived digital competences of Romanian pre-tertiary cycle teachers about their professional status, school location, gender, age, taught field, and prior participation in training for online teaching. Using data from 3,419 self-completed questionnaires in an online survey of teachers performed at the beginning of the global lockdown in March 2020, we have built two reliable measures of perceived digital skills, namely the Self-Assessed Multimedia and Online Skills Score (SMOS) and the Self-Assessed Digital Office Skills Score (SDOS), which were the dependent variables in our study. Hierarchical linear regressions were used to test the hypotheses regarding the variations of dependent variables, measuring the two concepts of self-assessed digital skills (SMOS and SDOS). These concepts underlined that both decrease with age and are positively affected by prior attendance at training sessions for online teaching skills and by having ICT and informatics as a taught subject field. However, teachers of all specialties are relatively significantly less skilled in this field. The most important results concern the impact of gender and professional status on the teachers’ self-assessed digital competences. In summary, it appears that self-assessed office digital skills are a specialism demonstrated mainly by female teachers, while multimedia and online skills are perceived by teachers to be a “male” domain. Simultaneously, net of the other variables, a higher status within the teaching profession correlates positively with perceived office digital skills. Lastly, implications for future research, as well as for educational interventions and policies, are discussed.