Industrial production has brought increased wellbeing in the last years, but the amount of solid waste has undoubtedly increased. Thus, open dumpsites and landfills have been created throughout the world, with serious impacts on the environment and public health. In such a context, occupational health and safety (OHS) issues related to workers that have to deal with landfill characterization or management have not been considered sufficiently. To reduce such a research gap, in 2019 a research project started in Italy on OHS risk assessment in landfills. In fact, in such facilities, workers can be subjected to direct contact with the polluted environment and might not be completely aware of the entity and type of pollution (e.g., in open dumpsites). Starting with the analysis of INAIL data on accidents at work which occurred in Italy during the period 2008–2019, a specific risk analysis was carried out with the goal of defining risk determinants and profiles by means of K-means cluster analysis. Such an analysis allowed us to recognize the use of work equipment and the work environment as the main determinants of the accidents on the one hand, and the “driver of the excavator” as the most risky activity on the other. The achieved results take a step forward towards the characterization of occupational health and safety issues in landfills. Accordingly, the research outcomes represent a basis on which to address further research work in this field.