Silicon is one of the most abundant elements in the Earth’s crust and, although it is not an essential element for plant growth, it is considered beneficial as it can help in defense against biotic and abiotic stresses. Research on the effects of foliar sprays containing silicon has been well documented for different plants. However, in olive plants there is considerably less research focused on silicon soluble foliar formulations, which differs from the application of inert materials, like kaolin. The purpose of this study was to evaluate the effects of three increasing levels of foliar-applied soluble silicon on the characteristics of olive fruit and olive oil parameters. Fruit morphology, contents of multiple polyphenols, fatty acid profiles and mineral content in olive oil, olive oil quality parameters, fruit yield, and olive oil production parameters were assessed. Results show significant effects of silicon treatments on palmitic, palmitoleic, and linoleic acids and on the content of mono- and polyunsaturated fatty acids. Polyphenols were generally more influenced by the cultivar rather than by silicon. Apigenin, phenolic acids, and flavonoids were impacted by silicon treatments. Fruit morphology was affected by silicon treatment and, generally, parameters (fruit and seed length, width, and mass) increased at higher silicon application. This was concomitantly seen in both fruit and extra virgin olive oil (EVOO) yield increase, but only for the Leccino cultivar, suggesting specific cultivar x treatment interplay for those traits. Increases in mineral contents in olive oil due to Si treatments were not found, except for silicon, where Si2 and Si3 treatments yielded higher silicon content in olive oil compared to control. Results of this study indicate that Silicon Foliar Application could be used to enhance olive yield and only slightly modifies the fatty acid composition of olive oil and the content of some of the phenols. Although silicon application did affect several parameters, the effect of cultivar was more pronounced in affecting most of the parameters. Further research could be driven towards the effect of foliar silicon on these parameters under environmental stress factors.