The purpose of the study was to clarify the relationship between patterns of habitual coping strategies and health. In accordance with the literature, we expected flexibility of coping styles to be associated with beneficial health-related outcomes. In a cross-sectional design a frequently applied stress coping questionnaire (SVF) with five subscales and an additional self-developed scale served to assess habitually applied coping strategies. Health-related outcome measures consisted of ICD-10 diagnoses and various self-rating instruments. A total of 145 teachers with relatively homogeneous but elevated levels of professional strain participated in the study. Data analysis relied on hierarchic (Ward) and iterative (k-means) cluster analyses as well as on ANOVAs. The analysis identified three coping clusters with high internal stability called flexible compensation, inconsistent compensation, and ruminative self-isolation. Inspection of the clusters revealed their association with health-related variables. Most beneficial values were found in the flexible compensation group regarding ICD-10 diagnoses, well-being, job satisfaction, depression, burnout and subjective prognosis of gainful employment, confirming our expectations. Inspection of coping patterns contributes to the identification of health-related outcomes. An analysis of coping patterns instead of single coping strategies may widen our perspective on the relationship between occupational stress and health.