Landscape composition not only affects a variety of arthropod-mediated ecosystem services, but also disservices, such as herbivory by insect pests that may have negative effects on crop yield. Yet, little is known about how different habitats influence the dynamics of multiple herbivore species, and ultimately their collective impact on crop production. Using cabbage as a model system, we examined how landscape composition influenced the incidence of three specialist cruciferous pests (aphids, flea beetles, and leaf-feeding Lepidoptera), lepidopteran parasitoids, and crop yield across a gradient of landscape composition in New York, USA. We expected that landscapes with a higher proportion of cropland and lower habitat diversity would lead to an increase in pest pressure of the specialist herbivores and a reduction in crop yield. However, results indicated that neither greater cropland area nor lower landscape diversity influenced pest pressure or yield. Rather, pest pressure and yield were best explained by the presence of non-crop habitats (i.e., meadows) in the landscape. Specifically, cabbage was infested with fewer Lepidoptera in landscapes with a higher proportion of meadows likely resulting from increased parasitism. Conversely, cabbage was infested with more flea beetles and aphids as the proportion of meadows in the landscape increased, suggesting that these pests benefit from non-crop habitats. Furthermore, path analysis confirmed that these landscape-mediated effects on pest populations can have either positive or negative cascading effects on crop yield. Our findings illustrate how different pest species within the same cropping system show contrasting responses to landscape composition with respect to both the direction and spatial scale of the relationship. Such tradeoffs resulting from the complex interaction between multiple-pests, natural enemies, and landscape composition must be considered, if we are to manage landscapes for pest suppression benefits.