Despite the importance of flowering for fruit formation, it has been considered very little in breeding programs involving fruit species, including olives. We evaluated the principal morphological flower-quality components in the olive cultivars, ‘Arbequina’ and ‘Picual’, and in the progenies of their crosses. Wide ranges of variation were obtained for all the inflorescence traits and ovary tissue sizes. An analysis of variance indicated that the residual error was the main contributor to the inflorescence traits, except for the number of perfect flowers, underlining the need to evaluate adequate numbers of inflorescences for accurate measurements of these traits. However, the high repeatability obtained for the inflorescence traits suggests that simple evaluation procedures could be accurate enough for genotype characterization. The average values for ‘Arbequina’ were in the upper range for all the traits; the opposite occurred for ‘Picual’, and the values for most of the progenies were intermediate. No significant differences between the maternal and paternal effect on inheritance were found. Some interesting transgressive segregants showed a higher flower number, greater ovary and mesocarp size, or percentage of ovaries with all four fully developed ovules. The correlations among the parameters may have reflected a relatively consistent distribution of the ovaries’ structural components and a close relationship between the ovaries and their mesocarp growth.