The paper focuses on the seasonal oil accumulation in traditional and super-high density (SHD) olive plantations and its modelling employing image-based linear models. For these purposes, at 7-10-day intervals, fruit samples (cultivar Arbequina, Fasola, Frantoio, Koroneiki, Leccino, Maiatica) were pictured and images segmented to extract the Red (R), Green (G), and Blue (B) mean pixel values which were re-arranged in 35 RGB-derived colorimetric indexes (CIs). After imaging, the samples were crushed and oil concentration was determined (NIR). The analysis of the correlation between oil and CIs revealed a differential hysteretic behavior depending on the covariates (CI and cultivar). The hysteresis area (Hyst) was then quantified and used to rank the CIs under the hypothesis that CIs with the maximum or minimum Hyst had the highest correlation coefficient and were the most suitable predictors within a general linear model. The results show that the predictors selected according to Hyst-based criteria had high accuracy as determined using a Global Performance Indicator (GPI) accounting for various performance metrics (R2, RSME, MAE). The use of a general linear model here presented is a new computational option integrating current methods mostly based on artificial neural networks. RGB-based image phenotyping can effectively predict key quality traits in olive fruit supporting the transition of the olive sector towards a digital agriculture domain.