The segetal flora of winter crops includes mostly native or archaeophyte annual species that are often strong specialists of their habitats. Threatened by the intensification of agriculture, segetal flora is particularly valuable from a perspective of biodiversity conservation and evolution. Moreover, it contributes to maintain biodiversity in agroecosystems and provides several ecosystem services. The dataset here described was set up to provide the first inventory of the segetal flora of Italian winter cereal crops and allied crop types, the latter including flax and autumn-sown legumes. It includes 24,676 georeferenced occurrence data deriving from 1,240 floristic and phytosociological relevés. The data were collected from the greater part of Italian territory, in a temporal range spanning from 1946 to 2018.