Cold temperature during winter season consider an environmental constrains for root and shoot development of olive cuttings. This experiment was carried out during two seasons (2018/19 and 2019/20) to study the rooting ability of  ‘Coratina', ‘Picual' and ‘Manzanillo' olive cultivars in addition to study the effect of supplementary intermittent application of IBA and antioxidant (1:1 ascorbic and citric acid) at 100, 200, 300ppm three times after cuttings  planting on their rooting behavior during cold winter. The results showed that, ‘Coratina' olive cultivar recorded the highest significant rooting percent success (75.86 &74.73%) and root number compared to ‘Picual' and ‘Manzanillo' cultivar. While, ‘Manzanillo' cultivar recorded the lowest rooting percent, root number and root length. Antioxidant at 300ppm recorded the highest rooting percent 74.44 & 73.78%, root number and root length. Concerning the interaction effect, the highest significant rooting percent 94.67 & 96.00% and root number was achieved by ‘Coratina' olive cultivar treated with 300 ppm antioxidant. While, the highest root length recorded by ‘Coratina' cultivar with100ppm IBA and the highest leaves number recorded by ‘Manzanillo' cultivar under 100 ppm antioxidant. It can be concluded that, ‘Coratina' olive cultivar was more suitable for winter season propagation. Also, supplementary application of 300ppm antioxidant was more effective in olive cuttings propagating, while 300ppm IBA had negative effects.