In the Northwestern region of Russia, and in the Leningrad Region in particular, mass outbreaks of aphids occasionally occur, which have a significant impact on crop formation. The aim of the study was to investigate the species composition, complex structure, and population dynamics of aphids in the fields of a grain-grass-row crop rotation, which is widely practiced in this territory. The aphid complex was studied during 2021–2022 using yellow water traps placed in all fields of the crop rotation. Aphid counts were carried out at 7–8 day intervals, resulting in a total of 10 and 15 counts in 2021 and 2022, respectively. The aphid complex of the graingrass-row crop rotation was characterized by high species diversity (30 species) but low abundance (1.9 individuals/trap), which varied depending on the agrocoenosis characteristics within a range of 1.3–2.8 individuals/trap, on average, over the crop growing season. The agrocoenoses differed considerably in the composition and structure of their aphid complexes, except for those whose cultivated plants belonged to the same botanical family and had identical seasonal development patterns (winter rye, perennial grasses). The numerical majority consisted of species whose feeding specialization is associated with cultivated plants (85.3%), with the remainder accounted for by weed species (12.6%) and woody and shrub vegetation (2.1%). The maximum aphid abundance in the crop rotation was recorded in the second decade of June, which coincided with the mass outbreak of the bird cherry-oat aphid in spring oat crops, and to a lesser extent in winter rye and perennial grass stands.