The cypsela morphology and anatomy of seven genera and 15 species of the tribe Cichorieae were studied using LM and SEM microscopy. These genera are Cichorium L., Koelpinia Pall., Lactuca L., Hyoseris L., Reichardia Roth, Sonchus L. and Taraxacum F.H.Wigg. Systematically, the cypsela pericarp shows valuable variation. A description of cypsela features, SEM micrographs showing the sculpture, epidermal cells, anticlinal and periclinal cell walls, and the secondary structures; line drawings of cross sections using camera Lucida focusing on the sectional configuration and cellular variations, especially the mesocarpic region; and an artificial key to the investigated taxa based on cypsela morphology and anatomy are provided. Morphological and anatomical criteria concerned with cypsela were investigated, and the relationships between the investigated taxa were discussed; these criteria were used significantly for classification and differentiation between the studied species. The presence or absence of wings, ribs, and the presence or absence of parenchyma or libriform fibers used as key characters for differentiation between the investigated taxa. The features of shape, margins, and sculpture of epidermal cells can distinguish between some closely related species of studied Sonchus species. Nevertheless, the shape of sections and layers of libriform fibers and parenchyma are useful features for the identification of several species.