Quality characteristics of olive products significantly depend on cultivar (cv), among other factors. In this study, seven traditional, noncommercial Greek cultivars, along with the commercial Spanish Arbequina cv., were examined for the phenolic antioxidant dynamic of their leaves. Polar extracts (aqueous, methanol, and ethanol) were analyzed for Total Phenol (TP), Flavonoid (TFL), Hydroxycinnamic Acid Derivatives (THAD), Flavonol (TFLVN) contents, DPPH radical scavenging ability, and Ferric Reducing Capacity (FRAP). Selective characteristics of olive leaf methanol extracts for all cultivars were re-examined on a second sampling period. Olive leaf is considered a rich source of phenolic antioxidants total phenol content reaching 29.3 ± 1.3, 30.6 ± 0.4, and 27.0 ± 1.1 mg caffeic acid/g dry leaf for aqueous, methanol, and ethanol extracts, respectively) and all cultivars were considered of equal bioactive dynamic. TP data derived from Folin–Ciocalteu and another spectrophotometric assay employed presented a high correlation for all examined cases (R2 = 71.5–86.9%). High correlation (R2 = 0.92) was also found between TP and FRAP findings of aqueous extracts. Olive leaf is considered a promising source of phenolic antioxidants irrelevant to cultivar and therefore even cultivars less effective for oil or table olive production could be efficiently exploited for the bioactive dynamic of their leaves.