This study was an investigation of prevalence and associations between self-rated health and working conditions for small-scale enterprisers in a county in Sweden. A postal questionnaire was answered by 340 male and 153 female small-scale enterprisers in different sectors, with a response rate of 66%. For comparative purposes, data from a population study of 1,699 employees in private companies was included in the analyses. Differences were tested by Chi²-test and associations were presented as odds ratios (OR) with a 95% confidence interval (95% CI). The frequency of health problems in male enterprisers was higher than in employees in the private sector, while the frequency of health problems in female enterprisers was equal to that of the control employees. The main findings highlighted that male enterprisers reported higher rate of health problems and female enterprisers equal rate compared with employees in the private sector. Enterprisers stated musculoskeletal pain (women 59%, men 56%) and mental health problems (women 47%, men 45%) as the most frequent health problems. Poor job satisfaction, reported by 17% of the females and 20% of the male enterprisers, revealed an OR of 10.42 (95% CI 5.78-18.77) for poor general health. For the enterprisers, the most frequent complaints, musculoskeletal pain and mental health problems, were associated with poor job satisfaction and poor physical work environment. An association between poor general health and working as an enterpriser remained after adjusting for working conditions, sex and age.