In Portugal., the study of mechanical pruning in olive orchards began in 1997. Trials were carried out in traditional orchards, and the obtained results revealed that mechanical pruning can contribute to the reduction in pruning costs without a reduction in yield. In 2005, the authors started an evaluation of mechanical pruning in high-density olive orchards. The trial was organised in a randomised, complete block design, with three replications. Four treatments were compared: T1—manual pruning, using chain saws in 2005, 2010, 2014, and 2017; T2—mechanical pruning, topping, and hedging (two sides) in 2014 and 2017, followed by manual pruning complement; T3—mechanical pruning, topping in 2005, topping and hedging (west side) in 2008 and 2012, topping and hedging (east side) in 2010, 2014 and 2017, summer topping in July 2015, and hedging (west side) in winter 2016; T4—mechanical pruning, topping in 2005, topping and hedging (two sides) in 2010, 2014, and 2017, and summer topping in July 2015. The average yield per tree for each treatment was evaluated. In the first period (5 years), no significant differences were found between treatments. In the second period (4 years), a greater frequency of mechanical pruning (T3) showed a lower yield, with significant differences with treatment T2. In the third period of 5 years, a greater pruning severity reduced the olive yield (2014). Manual pruning complement after mechanical pruning (T2) did not increase olive yield; however, the average yield over this period of time was similar. The olive yield was maintained over a period of 14 years by only applying mechanical pruning, without manual pruning complement inside the canopy.