Objectives: The aim was to evaluate job satisfaction, challenging encounters and work-related outcomes in dentistry and their association with the work-related outcomes scales ‘burnout inventory’, ‘general life satisfaction’ and ‘cognitive stress symptoms’. Methods: This cross-sectional study was based on the results of a questionnaire administered to a sample of 1,811 dentists in the German federal state of Schleswig-Holstein. Besides sociodemographic data and practice characteristics, topics such as challenging patient traits and job satisfaction, and three work-related outcome scales, were evaluated. Descriptive statistics and linear regression analyses were computed to explore potential associations with the three work-related outcome scales. Results: A response rate of 35.2% (638/1,811 participants) was observed for this study. Dentists described that 25% of their patients were challenging. The highest rate was found for ‘aggressive patients’ and the lowest rate for ‘anxious patients’. The proportion of challenging patient traits was significantly correlated with the three work-related outcomes whereby the highest significant correlation was observed for ‘burnout inventory’. Conclusions: As shown by our results, the higher perception of the proportion of anxious patients, the higher the risk of burnout. Therefore, special management of the treatment of anxious patients is necessary, which could have a positive implication on the perceived work-related stress. A crucial aspect for well-being at work as a dentist (besides job satisfaction and work-related aspects) is the evaluation of what kind of patients result in a challenging encounter.