The evolution of asymmetric genitalia is a common and recurrent phenomenon in a wide variety of insect taxa. However, little is understood about the evolution of left-right asymmetry in reproductive structures. Since a better knowledge of it could have an important impact on the study of genital evolution, in the present study we investigate the phylogenetic and evolutionary patterns of asymmetric male genitalia in Cyclocephalini. We use a Procrustes distance based method for quantifying asymmetry. Analysis of 119 species belonging to 14 genera revealed a diverse array of asymmetries with a strong indication that asymmetries are more strongly developed in the terminal part of the aedeagus. Further, we find that asymmetries have evolved repeatedly within this small taxon. Micro-CT scans, a technique not employed before in studies of genital asymmetry, are made of several symmetric and asymmetric species. This reveals unexpected asymmetric sclerotised structures inside the otherwise symmetric aedeagus of Cyclocephala amazona, which underlines that asymmetries are not restricted to the exterior of the male genitalia but are also found internally.