Retrospective assessment of agricultural workers’ pesticide exposure is essential for understanding and establishing links between their activities throughout their careers and the potential onset of serious work-related conditions such as cancer or neurodegenerative diseases. There are few reliable tools supported by a precise and structured methodology for documenting occupational exposure histories. The cultivation of export bananas, or dessert bananas—one of the most widespread crops in the French West Indies—spans the entire year and necessitates the use of numerous plant protection products (PPPs) to which agricultural workers are exposed. No previous study has estimated the number of these workers, characterized their PPP exposures over time, or identified the health effects associated with these exposures. We used three tools, two of which were developed in-house, to answer the question: Which PPPs have been applied to banana cultivation over the past decades, and what are their health effects? The first tool is the construction of a crop-exposure matrix (CEM) specific to dessert banana cultivation in the Caribbean, through which we identified all PPPs used on this crop since the 1960s, as well as the frequency and probability of their use. The second tool is the development of the CipaTox database; it was established to identify known or suspected health effects associated with chronic exposure to the active ingredients (AI) of PPPs registered in France since 1961. A focus was placed on carcinogenicity, mutagenicity, and reproductive toxicity (CMR), as well as on potential endocrine-disrupting effects (EDEs). Finally, the third tool, provided by the Ministry of Agriculture, consists of the agricultural censuses (ACs) from 1981, 1989, 2000, and 2010, which enabled us to identify the sociodemographic characteristics of banana workers in the French West Indies. By cross-referencing these three data sources, we calculated the prevalence of occupational exposure for the four years covered by the RA to PPPs used on bananas in the French West Indies and identified the health effects they may cause. Our findings show that from 1981 through 2010, all banana workers in the Caribbean—whose numbers fell from 13,504 to 5,270 individuals—were exposed to at least one substance harmful to health and classified as CMR or PE. In 2015, the prevalence of exposure to CMRs and PEs among banana workers in the Caribbean remained at 100%, with all farms using at least one active ingredient classified as a CMR or PE. The specific characteristics of agriculture in the Caribbean must be taken into account when assessing workers’ exposure to PPPs. Indeed, the hot and humid climate, on the one hand, allows for continuous dessert banana production throughout the year and, on the other hand, fosters significant pressure from pests, diseases, and weeds, necessitating the regular use of PPPs to ensure the production of export-quality bananas. Our research helps guide prevention efforts for agricultural professionals by enabling them to identify substances with adverse health effects. It calls for the implementation of several measures, including the promotion of alternative banana production methods, the limitation of PPP use, the restriction of PPPs classified as CMR or PE, raising workers’ awareness of these risks through prevention campaigns, and finally, providing information and training to general practitioners and occupational health professionals to facilitate the recognition of occupational diseases.