Although small-scale enterprises (SSEs) dominate the private enterprise sector, knowledge about support for these organizations from occupational health services (OHSs) is insufficient. The aim of this research was to study OHS services provided and staff cooperation with SSEs in Norway and Sweden. In total, 87 Norwegian and 51 Swedish OHS providers answered a survey on their experiences providing requested services from and cooperation with SSEs. Based on survey questions and constructed indices, providers in the two countries were compared using independent sample t tests and non-parametric tests. Open-ended questions were analyzed using qualitative content analysis. The results showed that SSEs, particularly in industrial, construction, and trade sectors, commonly contract for Norwegian and Swedish OHSs, and these contracts have increased in the last 12 months. Norwegian providers state that SSEs request broader organizationally- based services; their Swedish counterparts request more individual-based health-related services. Improvements concerning specific strategies for OHS collaboration with SSEs may be needed.