Phenolic compounds from jujube fruits and related antioxidant activities were investigated during the ripening stages. Three different antioxidant assays, including ORAC, FRAP and DPPH, were monitored on crude jujube extract (CJE). Jujube fruits were additionally fractionated into three selective fractions F1, F2, and F3. However, only the FRAP assay gave the relative antioxidant activity for the three fractions. Furthermore, HPLC-ESI-MSMS (Q-Tof) and GC-MS were used to identify the compounds in each purified fraction. Using FRAP, F1 mainly composed of lipids, exhibited the lowest antioxidant activity (?0.080 ± 0.015 mmol trolox/100 g, p < 0.05). F2, rich in flavanols and flavonols, displayed 50-fold higher activity (4.27 ± 0.11 mmol trolox/100 g). Remarkably, F3 with an elevated content of condensed tannins (polymeric proanthodelphinidins), exhibited the highest antioxidant activity (25.4 ± 0.35 mmol trolox/100 g). The presented results showed that the phenolic profiles of the fruits were influenced by their developmental stage. Furthermore, during ripening, the antioxidant activity may be more impacted by the flavanols and condensed tannins. The purified condensed tannins of jujube fruits may be used as natural antioxidant extracts.