Résumé : The cocoa bean shell (CBS) is one of the main cocoa byproducts with a prospective to beused as a functional food ingredient due to its nutritional and sensory properties. This study aims todefine the chemical fingerprint of CBSs obtained from cocoa beans of diverse cultivars and collectedin different geographical areas of Venezuela assessed using high-performance liquid chromatographycoupled to photodiodes array and mass spectrometry (HPLC-PDA-MS/MS) and spectrophotometricassays combined with multivariate analysis for classification purposes. The study provides a comprehensive fingerprint and quantitative data for 39 compounds, including methylxanthines and severalpolyphenols, such as flavan-3-ols, procyanidins, and N-phenylpropenoyl amino acids. Several keycocoa markers, such as theobromine, epicatechin, quercetin-3-O-glucoside, procyanidin_A pentoside_3, and N-coumaroyl-L-aspartate_2, were found suitable for the classification of CBS accordingto their cultivar and origin. Despite the screening methods required a previous purification of thesample, both methodologies appear to be suitable for the classification of CBS with a high correlationbetween datasets. Finally, preliminary findings on the identification of potential contributors forthe radical scavenging activity of CBS were also accomplished to support the valorization of thisbyproduct as a bioactive ingredient in the production of functional foods.