The SIMDualKc model was used to simulate crop water requirements for a super high density olive orchard in the region of Alentejo, Portugal. This model uses the dual crop coefficient approach to estimate and partitioning the actual crop evapotranspiration (ETc act) and therefore to perform the soil water balance. The model was calibrated with 2011 tree transpiration using trunk sap flow measurements and was validated using similar data from 2012 and tested with 2013 data. Low root mean square errors (RMSE < 0.53 mm·d−1) and acceptable modelling efficiency indicators (EF > 0.25) were obtained. Further validation was performed comparing modelled ETc act with eddy covariance measurements. These indicators support the appropriateness of using SIMDualKc to guide irrigation management. The basal crop coefficient (Kcb) curves obtained with SIMDualKc for those 3 years were compared with the Kcb values computed with the Allen and Pereira approach (A&P approach) where Kcb is estimated from the fraction of ground cover and plant height considering an adjustment factor for crop stomatal control (Fr). Fr values were obtained through a trial and error procedure through comparing the Kcb estimated with this approach and with SIMDualKc. The Kcb curves obtained by both methods resulted highly correlated, which indicates that the A&P approach may be used in the irrigation management practice to estimate crop water requirements. Results of performing the soil water balance with SIMDualKc have shown that soil evaporation is a large fraction of ETc act, varying between 41% and 45% for the 3 years under study. Irrigation, applied with a drip system, represented 39 to 56% of ETc act, which shows the great importance of irrigation to achieve the water requirements of super intensive olive orchards. Nevertheless, the analysis has shown that the irrigation management adopted at the orchard produces a water deficit larger than desirable, with a ratio of ETc act to non-stressed crop evapotranspiration (ETc) varying from 70% to 94% during the mid-season, when that ratio for a eustress irrigation management could be around 90%.