The effect of different strategies and the time of pruning on olive vegetative-reproductive behavior was studied in a 5-year-old high-density orchard (1,250 trees ha−1, cv. ‘Ascolana tenera’). The treatments were: a) winter lateral pruning and topping, b) summer lateral pruning and winter topping, c) winter lateral pruning and summer topping and d) summer lateral pruning and topping. Selective spring pruning maintaining a conical shape of the canopy was used as the Control. Topping significantly maintained tree height recorded at the end of the 3-year trial in comparison to the Control (3.84 ± 0.45 m), in particular summer treatments maintained the final tree height at 3.0 ± 0.26 m. Summer topping and lateral pruning significantly reduced canopy volume compared to winter pruning and the Control. There was less vegetative re-sprouting in the control and, on the average, less for summer than for winter pruning in the same year of pruning. There were no significant differences between the treatments regarding the seasonal vegetative growth of 1-year-old mixed shoots. Fruit yield per tree was significantly higher with time-split pruning (part in winter and part in summer) with respect to conical-shape pruning of the canopy. Results suggest that the proposed management of pruning with winter lateral pruning and summer topping contributes to good vegetative-reproductive balance of young trees with high yield and a more compact shape.