Olive oil has gained much appreciation among consumers worldwide leading to increased markets as well as greater consumer expectation and thus more challenges for the relevant food sector. By understanding the product, its interactions with the environment and the protective role of the package, decisions can be made on the barrier properties required of the packaging materials to achieve the desired shelf-life. To this end, the shelf-life of packaged olive oil under various storage and distribution environments can be predicted by mathematical modeling. This review examines the basic factors affecting the shelf-life of olive oil in different packaging systems and describes the main oxidative degradation mechanisms for them. Since an experimental investigation to correlate the basic quality factors and the shelf life of a product is time- and effort-consuming, the use of mathematical modeling for the prediction of packaged olive oil shelf-life is also discussed. In the presented works the shelf-life predictions were based on the most consumer related attributes i.e. on the evolution of olive oil flavour compounds under various packaging and storage conditions. The validation of the simulations against known experimental results, showed a very good correlation, confirming the great value of the mathematical approach for a quick and accurate prediction of oxidation sensitive products’ shelf life.