Over the past decade, Halyomorpha halys has become one of the main threats to hazelnut production. Its trophic activity makes kernels inedible due to strongly detrimental effects on the organoleptic quality. Its management in Italy is still tricky due to the lack of effective native biocontrol agents and authorized and effective insecticides. A field test was performed on San Giovanni (SG) and Tonda Romana (TR) cultivars (early and late ripening, respectively) to assess the intensity of cimiciato damage with different pest management approaches (no insecticide and integrated pest management, IPM). Moreover, phenological analysis of fruits and the monitoring of stink bug species by traps and plant beating were carried out. In the untreated plots, the SG cv showed a higher cimiciato incidence with respect to the late TR cv (40% SG–NI vs. 23% TR–NI). This was probably due to the different phenological phases in which stink bugs injured the fruits. In fact, stink bug bites provoke different kinds of injuries (blanks, shriveled, and cimiciato) according to the fruit’s development period. Indeed, in the period of highest insect occurrence in the field, the fruits of the early cv (SG) were in kernel expansion, a phenological phase in which bug injuries are more likely in cimiciato defects. Lastly, the IPM did not provide sufficient fruit protection (19% SG–IPM vs. 11% TR–IPM). The interaction between the phenological development of hazelnuts and the brown marmorated stink bug represents a critical aspect in understanding and implementing effective strategies for controlling this key pest on hazelnut trees.