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The olive oil content in phenolic compounds depends on the variety of the fruit used for its extraction as well as on the predominant climate conditions in the tree cultivation area. Here, we report on the characterization of virgin olive oil samples obtained from fruits of the main Tunisian olive cultivars Chemlali and Chetoui, grown in three different Tunisian locations, Zaghouan (North), Sousse (Center) and Sfax (South). Chetoui olive oil samples obtained from fruits of olive trees cultivated in Zaghouan and Chemlali olive oil samples obtained from fruits of olive trees cultivated in Sousse were found to have a higher mean total phenol content (1004 and 330 mg/kg, respectively). Olive oil samples obtained from fruits of both cultivars had different phenolic profiles and a higher content in 3,4-DHPEA-EDA when the olive trees were cultivated in Zaghouan. Both olive cultivars were found to have different responses to environmental conditions. Chetoui olive oil showed decreased oxidative stability when the fruits were obtained from olive trees cultivated in the center of Tunisia (34.8 h) and in Sfax (16.17 h). Furthermore, statistical data showed that the phenolic composition and oxidative stability of Chetoui olive oil varied more by location than those of Chemlali olive oils.