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Olive anthracnose caused by the hemibiotrophic fungal pathogen <i>Colletotrichum acutatum</i> is a serious threat to the olive sector. Olive oil and fruit production is severely constrained by <i>Colletotrichum</i> spp. infection, being <i>C. acutatum</i> the most distributed pathogen in Portuguese olive orchards. To understand the impact of <i>C. acutatum</i> on phenylpropanoids biosynthesis, the enzyme activity, phenolic compounds, <i>ortho</i>-diphenols, and flavonoids content were determined and correlated with the expression of gene encoding key enzymes within phenylpropanoids metabolism in susceptible and tolerant olive fruits, during maturation and when infected with <i>C. acutatum</i>. Differences between cultivars was observed, the tolerant olive cv. Picual presented a higher basal value and a stable phenolic content throughout the infection process, supporting its high <i>C. acutatum</i> tolerance, whereas in the susceptible olive cv. Galega these secondary metabolites were significantly increased only after the elicitation with <i>C. acutatum</i>.