Aims: Four different measures of sickness absence were related to psychosocial and physical work characteristics in workplaces with high, intermediate, and low sickness absence. The relationships between work characteristics and sickness absence were hypothesized to differ depending the sickness absence measure used. Methods: Questionnaire data on physical work environment, physical load, support, influence at work, and worry were collected from 1,726 employees at 48 dental clinics in Stockholm, Sweden and were related to registry-based sickness absence obtained at the workplace level. The sickness absence measures included: (1) frequency, (2) one-day absence, (3) overall duration, and (4) duration between 2 and 21 days. Results: For frequency, significant differences were found for all work characteristics, with poor work characteristics being associated with a high frequency of sickness absence. Considering duration between 2 and 21 days, there were significant differences in support, influence at work and physical work environment; for one-day absence, support, influence at work and physical load differed significantly. Conversely, there were no significant differences for the overall duration measure. Conclusions: The results show that frequency of sickness absence is most consistently related to work characteristics, that short-time sickness absences have more inconsistent relationships and that relationship with overall duration is lacking. This highlights the need for further differentiation between different sickness absence measures, the behavioral patterns associated with different types of absences and the implication of such processes for prevention and intervention.