An increase in olive oil consumption has occurred worldwide in the last decades and has resulted in more land area being dedicated to olive orchards in several southern hemisphere countries. In order to achieve sustainable productivity under the increasing water scarcity, optimal water use is essential. Thus, a field experiment was conducted during four consecutive growing seasons (2010-2011 to 2013-2014) to evaluate olive oil quality in response to irrigation cut-off strategies applied after fruit set using midday stem water potential (Psi(stem)) thresholds in a super-high density olive orchard (cv. Arbequina) located in the Pencahue Valley, Maule Region, Chile. The experimental design was completely randomized with four treatments and four replicates. In treatment T-1 (control), Psi(stem) was between -1.4 and -2.2 MPa (100% of actual evapotranspiration) throughout the season, while the T-2, T-3 and T-4 treatments did not receive irrigation from fruit set until they reached a Psi(stem) threshold of approximately -3.5, -5.0, and -6.0 MPa, respectively. Once these thresholds were reached, irrigation was reestablished and maintained as T-1 in all treatments until olives were harvested. Fruit oil and water content (%) at harvest were not affected by the different treatments. Free acidity was also not affected, while peroxide and extinction coefficients only showed minor differences between treatments that were within the limits established for commercial extra virgin oil quality. Total polyphenols at harvest were much higher in the water deficit treatments and showed a significant linear relationship each year with the water stress integral. The percentages of the main fatty acids were not affected by the treatments. However, they were significantly different between seasons. Sensory tests indicated that the higher total polyphenol content positively contributed to more pronounced bitter and pungent attributes of olive oil from trees with higher water deficit. Thus, the irrigation cut-off strategies evaluated at our four-year study can be an excellent management tool to both improve the oil quality of cv. Arbequina and reduce water use in super-high density orchard.