Continuous monitoring of the tree water status will enhance irrigation performance, particularly when applying deficit schedules. The olive tree is a highly drought-resistant species and management of the water stress could increase water savings. Trunk diameter fluctuations can be displayed as daily curves representing the shrinkage and swelling, and can provide information about tree water status. In olive trees, trunk growth rate (TGR) is the most useful indicator, but the daily variability reduced the commercial applications. Recently, weekly frequencies of TGR values were associated to the water status in one seasonal experiment. The aim of this work is to study the seasonal pattern and the interannual variations of these parameters in order to integrate them in an irrigation scheduling tool. The experiment was performed during two consecutive seasons (2018 and 2019) in a superhigh density mature olive orchard at Carmona (Seville, Spain). Three different irrigation scheduling treatments were considered in a randomized complete block design. The control treatment was fully irrigated with 150–175% crop evapotranspiration (ETc) in order to ensure an optimum water status. Regulated deficit irrigation-1 (RDI-1) was scheduled using only TGR data provided through the continuous measurements from a dendrometer. In this treatment, water stress conditions were controlled during the pit hardening period. RDI-2 was similar to RDI-1, but with a more severe water stress conditions during pit hardening and a maximum seasonal amount of water that limited rehydration. Water stress was greater during the 2019 season than the 2018 season, according to the midday stem water potential (SWP). Weekly frequencies of TGR values lower than −0.3 mm day−1 (Severe FR) and values between −0.1 and 0.3 mm day−1 (Good FR) described the water status pattern in the three treatments for both seasons. Only under severe water stress conditions (SWP more negative than −4 MPa) the values of these frequencies did not identify accurately the water status. However, the use of weekly frequencies of values greater than 0.3 mm day−1 (Alert FR) and the pattern of these Severe FR and Good FR themselves identified such conditions. The use of these three weekly frequencies (Severe, Good and Alert (SGA) approach) are suggested for continuous deficit irrigation scheduling in olive trees.