Olive growing is undergoing a transition from traditional cultivation systems to a more technological model characterized by increased mechanization and a higher density of plants per hectare. This shift implies the use of less vigorous varieties that can adapt to the new system. Most traditional varieties are highly vigorous, and breeding programs can provide solutions to this challenge. This study investigates the parental effect on different agronomic and olive oil characteristics and its role in breeding programs. The objectives were to evaluate and characterize different agronomic and olive oil traits in the progenies from 'Arbosana' × 'Sikitita' cross and its reciprocal cross 'Sikitita' × 'Arbosana'. The results showed a high variability of the characters evaluated in the progenitors of the reciprocal crosses. The highest coefficients of variation were observed in traits related to ripening index, phenolic compounds, polyunsaturated fatty acids, and Δ5-avenasterol, with phenolic content exhibiting the greatest variability. No statistically significant maternal effect was detected for any of the evaluated traits, although a slight positive maternal effect was systematically observed in the mean values of the evaluated traits. These results suggest that the maternal effect on olive is quite subtle, although due to a slight tendency of the maternal effect in the descriptive analyses, future studies are suggested to understand in depth the possible maternal effect on olive breeding.