The spermatozoa of spiders (Araneae) show a high structural diversity, resulting in several potential phylogenetic characters. In the present paper, we describe the spermatozoa of the spider family Pimoidae for the first time. We investigate four species of the genus Pimoa (P. altioculata, P. curvata, P. laurae, and P. edenticulata) by means of light and transmission electron microscopy. The male reproductive system consists of paired testes and long convoluted paired deferent ducts. The spermatozoa are generally characterized by: (1) a cylindrical acrosomal vacuole, (2) an acrosomal filament restricted to the precentriolar part of the nucleus, (3) a nuclear canal running in the periphery but projecting towards the posterior portion of the nucleus, (4) a short postcentriolar elongation of the nucleus, (5) a 9 0 axonemal pattern, and (6) cleistospermia as transfer form. The organization of the axoneme is of particular phylogenetic interest, since a 9 0 axonemal pattern was described within spiders only for the megadiverse family Linyphiidae, the sister group of Pimoidae. We have reconstructed the evolution of the axoneme using comparative spermatozoal data for 54 orbicularian species representing 11 families. We propose that the 9 0 axonemal pattern is a new synapomorphy for Pimoidae Linyphiidae. The phylogenetic and evolutionary implications of other potential sperm characters (e.g., length of the postcentriolar elongation of the nucleus) are discussed.