Research Highlights: This paper compares the thermal requirements in three different olive-growing areas in the Mediterranean region (Toledo, central Spain; Lecce, southeastern Italy; Chaal, central Tunisia). A statistical method using a partial least square regression for daily temperatures has been applied to study the chilling and heat requirements over a continuous period. Background and Objectives: The olive is one of the main causes of pollen allergy for the population of Mediterranean cities. The physiological processes of the reproductive cycle that governs pollen emission are associated with temperature, and thermal requirements strongly regulate the different phases of the plant’s life cycle. However, the point when several specific processes occur—Such as the phases within the dormancy period—Is unclear, and the transition between endodormancy and ecodormancy is not easily distinguishable from an empirical point of view. This work focuses on defining the thermal accumulation periods related to the temperature balance needed to meet the chilling and heat requirements for the metabolic activation and budbreak in olive trees. Results and Conclusions: Thermal accumulation patterns in olive trees are strongly associated with the bioclimatic conditions of olive-growing areas, and the olive flowering start dates showed significant differences between the three studied stations. Our results show that the chilling requirements were fulfilled between late autumn and early winter, although the chilling accumulation period was more evident in the coldest and most continental bioclimatic areas (central Spain). The heat accumulation period (forcing period) was clearly defined and showed a close relationship with the timing of olive flowering. Heat requirements were therefore used to generate accurate forecasting models to predict the beginning of the olive bloom and subsequent olive pollen emission. A forecasting model considering both the chilling and heat requirements was generated in Toledo, where the estimated days displayed an error of 2.0 ± 1.8 days from the observed dates. For Lecce, the error was 2.7 ± 2.5 days and for Chaal, 4.2 ± 2.4 days.