Water is essential for crops and plays a vital role in olive (Olea europaea) growth. Three irrigation treatments, rain-fed (CK), flood irrigation (FI), and drip irrigation (DI), were applied from late November to late May in a 2-year study (Nov. 2015 to Oct. 2017) on two olive cultivars, Coratina and Koroneiki. Shoot growth, flower and fruit characteristics, and olive and oil yields were measured. Compared with CK, FI had significantly higher values of vegetative growth, olive and oil yields, moisture content, and oil content. Although the fruit weight, pulp rate, and oil content with DI were the lowest, our results support that DI had the greatest positive effects on olive vegetative growth, flowers, fruit set, and olive and oil yields. It is suggested that DI in winter and spring is the best irrigation strategy for olive productivity in southwest China.