Quality of life (QoL) of dental professionals is a basic parameter of the quality of dental services (QS), a fact well-documented before and during the COVID-19 pandemic in different countries. This study is a comprehensive, cross-sectional survey aimed to explore possible differences in satisfaction from career and work-life integration, as well as QoL in a sample of Greek dentists during the second lockdown in March 2021. Methods: 804 dentists from the vast metropolitan area of Athens and Piraeus selectively responded by completing a self-reported questionnaire based on: the Copenhagen Questionnaire (CQ) for assessing work stress; the Maslach Burnout Inventory-Human Service Survey (MBI-HSS) for evaluating personal accomplishment; and the Quality-of-Life work scale (ProQOL-CSF). Data were analyzed using the independent -test, ANOVA, Pearson's correlation, and multiple linear regression. Results: QoL and career satisfaction were significantly diminished during the pandemic. Career satisfaction despite the pandemic was overall influenced in tandem by age (b = 0.427, = 0.001), marital status (b = 0.276, = 0.021), and inversely by years of practice (b = -0.330, = 0.007) and income (b = -0.221, = 0.015). Satisfaction from the work-life integration was influenced before the pandemic by marital status (b = 0.255 = 0.013), years of practice (b = -0.371, 0.0001), while gender, years of practice, age, higher education, and income played a significant role during the pandemic. QoL was impacted before pandemic by age (b = -1.007, = 0.001), number of children (b = -1.704, = 0.018), and higher degree (b = -1.143, = 0.001), while during the pandemic by gender (b = -0.582, = 0.002), number of children (b = 0.469, = 0.037), higher degree (b = 0.279, = 0.009), and years of practice (b = -0.523, = 0.0001). Males were more prone to low QoL, and dissatisfaction with career and work-life integration, during the pandemic. Income is a predictor of career satisfaction despite the pandemic. Personal resources through deep human relationships, higher education, beliefs, and values can offer a resilience shield against professional difficulties in periods of unexpected stressful events.