Citrus fruits exhibit a high level of different phytoconstituents, of which the changes in the different parts of the fruit during ripening have not been thoroughly studied yet. Thus, in this study, we have investigated how different parts of pomelo fruit (Citrus grandis L.) are modified throughout the development of two consecutive growing seasons. In detail, the main phytochemical compounds, such as total phenolic content, total flavonoid content, antioxidant capacity, DPPH free radical scavenging activity, Ferric reducing antioxidant power (FRAP), and naringin and tannin content, were analyzed. A systematic metabolism of these compounds was found during the development of the fruit, but some pomelo tissues showed a fluctuating trend, suggesting a dependence on the different growing season. Focusing on the tissue distribution of these compounds, the fruit membrane contained the highest level of total phenolic and flavonoid content; fruit flavedo displayed the highest antioxidant capacities and FRAP activities, whereas maximum accumulation of naringin was noticed in fruit albedo. Instead, the highest DPPH free radical scavenging activity and tannin contents were found in the pomelo juice. Regarding the distribution of compounds, a possible bias pattern for the accumulation of those compounds has been noticed throughout the fruit development. From the GC-MS analysis, a total of 111 compounds were identified, where 91 compounds were common in both seasons. Overall, these results could be useful for the food processing industry as guidelines for excellent quality foods and for introducing health-beneficial products and components into our daily diets.