Objectives: Shoulder disorders in the occupational environment have been widely studied, but the quality of research and methodology applied vary. Little has been done to ascertain whether shoulder pain in female repetitive workers is due to any verifiable pathology, or to compare findings with the general population. Therefore, we decided to evaluate the prevalence of self-reported shoulder pain in a group of female supermarket cashiers and in the general female population using a standardized questionnaire. Shoulder pain prevalence was then compared to imaging findings in order to assess specific and non-specific pain prevalence. Material and Methods: 196 cashiers and 302 controls filled in a standardized shoulder questionnaire and underwent an imaging examination of a shoulder. Results: The prevalence of shoulder pain was significantly higher in the group of cashiers (46.4%) than in the general population (25.5%) (OR = 1.821; 95% CI: 1.426–2.325). Specific pain prevalence was higher among the controls (19.5%) than among the cashiers (13.2%). Conclusions: The more frequent reports of shoulder pain in the supermarket cashiers are not correlated with a higher prevalence of imaging abnormalities. The causes of these more frequent complaints should be probably sought in the psycho-social and occupational environment.