In this study, four different kinds of table olive fermentations belonging to Olea europaea L. Itrana cultivar were evaluated: A, spontaneous fermentation; B, fermentation with a single inoculum (Lactiplantibacillus plantarum B1); C, fermentation with multiple inoculum (L. plantarum B1 + L. plantarum B51 + L. plantarum B124, 1:1:1); and D, fermentation with mixed (bacterium + yeast) inoculum (L. plantarum B1 + Candida boidinii). This research focuses on the correlation between the different mixes of inoculations and their effect under the chemical, sensorial, and textural profiles in the final products (olives) for potential applications on table olive fermentation. During the fermentation, some specific parameters were monitored: chemical characterization of oil fraction (pigments, tocopherols, fatty acids, alkyl esters, and sterol composition), Texture Profile Analysis (TPA), determination of olive color, and sensory evaluation of the final products. The use of LAB starters (single and multiple inocula) compared to spontaneous process revealed a greater performance in preventing the spoilage process and in developing favorable physico-chemical conditions during the fermentation. In fact, the highest values of fatty acid alkyl esters were reached in spontaneous fermentation (~480 mg/kg in jar A). The presence of C. boidinii as inoculum in jar D was involved in table olive softening: the fermented olives showed the lowest values of the parameters related to consistence of fruit as hardness (~2300 g) and gumminess (~990 g) and high value of fatty acid methyl esters (~110 mg/kg).