Risk assessments of chemical pesticides toward natural enemies are crucial for ensuring sustainable grapevine-integrated pest management. In this context, laboratory experiments were conducted to evaluate the toxicity of four insecticides (lambda-cyhalothrin, flupyradifurone, acetamiprid, and cyantraniliprole) and one fungicide (spiroxamine) commonly applied in German (European) vineyards on the pupae and adults of both Anagyrus vladimiri, a parasitoid of the vine mealybug Planococcus ficus, and Trichogramma evanescens, a parasitoid of the European grapevine moth, Lobesia botrana. The tested pesticides did not significantly affect the development of the pupal stage inside mealybug mummies or the emergence of the parasitoid A. vladimiri. The pesticides flupyradifurone, acetamiprid, and spiroxamine resulted in the highest mortality percentages for all emerged A. vladimiri parasitoids at 8 and 10 days after treatment compared with either in lambda-cyhalothrin or cyantraniliprole. However, all pesticides, except the diamide insecticide cyantraniliprole, significantly affected the development of the pupal stage and the emergence of the parasitoid T. evanescens. The percentages of T. evanescens emergence following the application of the fungicide spiroxamine or either lambda-cyhalothrin or flupyradifurone were significantly higher than those observed in the acetamiprid treatment. Regarding direct contact toxicity, the highest percentages (100%) of A. vladimiri adult parasitoid mortality were obtained in the flupyradifurone, acetamiprid, and spiroxamine treatments, while the lowest mortality percentages were observed in lambda-cyhalothrin, cyantraniliprole, and untreated control treatments. According to the IOBC classes of toxicity, flupyradifurone, acetamiprid, and spiroxamine were classified as harmful, while both lambda-cyhalothrin and cyantraniliprole were classified as slightly harmful to A. vladimiri adults. As such, all pesticides had a significant impact on the survival of exposed T. evanescens adults. The highest percentages of adult T. evanescens mortality were obtained in the flupyradifurone, acetamiprid, and spiroxamine treatments, with the fungicide spiroxamine resulting in significantly higher mortality percentages than either flupyradifurone or acetamiprid, while the lowest mortality percentages were found in the lambda-cyhalothrin and cyantraniliprole treatments. Therefore, applying the insecticides acetamiprid and/or flupyradifurone and the fungicide spiroxamine should be avoided when A. vladimiri and/or T. evanescens are naturally present or released in grapes. The insights gained from these two easy-to-rear parasitoid species allow analogous conclusions to be drawn for closely related species in vineyards belonging to either family Encyrtidae or Trichogrammatidae, which are not easy to rear. Interestingly, using the safer insecticides lambda-cyhalothrin and/or cyantraniliprole could be compatible with both parasitoid species, which could be sustainably exploited in either conservation or augmentative biological control in vineyards.