Based on observations for the beginning of the flowering stage of Malus domestica (apple) and Pyrus communis (pear) for the 1950–2018 period, phenological trends in north-eastern Belgium were investigated in function of temperatures during dormancy. Moreover, two different phenological models were adapted and evaluated. Median flowering dates of apple were on average 9.5 days earlier following warm dormancy periods, and 11.5 days for pear, but the relationship between bloom date and temperature was found not to be linear, suggesting delayed fulfilment of dormancy requirements due to increased temperatures during the chilling period. After warm chilling periods, an average delay of 5.0 and 10.6 days in the occurrence date of dormancy break was predicted by the phenological models while the PLSR reveals mixed signals regarding the beginning of flowering. Our results suggest overlapping chilling and forcing processes in a transition phase. Regarding the beginning of flowering, a dynamic chill model coupled to a growing degree days estimation yielded significantly lower prediction errors (on average 5.0 days) than a continuous chill-forcing model (6.0 days), at 99% confidence level. Model performance was sensitive to the applied parametrization method and limitations for the application of both models outside the past temperature ranges became apparent.