The geological history of the wasp superfamily Cynipoidea is reviewed, with the description of various new taxa, being mostly in Late Cretaceous amber from New Jersey and Canada. The various fossil lineages are incorporated into a phylogenetic analysis of the superfamily, and their implications for understanding the evolution of the group are explored. The following new taxa or taxonomic changes are proposed (authorship of all taxa is Liu and Engel): Protimaspidae, new family; Stolamissidae, new family; Stolamissus, new genus; Stolamissus mirabilis, new species; Proliopterinae, new subfamily; Proliopteron, new genus; Proliopteron redactus, new species; Goeraniinae, new subfamily; Goerania, new genus; Goerania petiolata, new species; Micropresbyteria, new genus; Micropresbyteria caputipressa, new species; Anteucoila, new genus; Anteucoila delicia, new species; Jerseucoila, new genus; Jerseucoila plesiosoma, new species; Syneucoila, new genus; Syneucoila magnifica, new species; Tanaoknemus, new genus; Tanaoknemus ecarinatus, new species; Kinseycynips, new genus; Kinseycynips succinea (Kinsey), new combination. The extinct family Rasnicynipidae is newly transferred to Figitidae and classified as a basal subfamily therein (Rasnicynipinae, status novus). The Gerocynipidae, its type genus Gerocynips, and the type species upon which they are founded, Gerocynips zherichini, are found to be nomenclaturally unavailable. Gerocynips zherichini is regarded as a nomen nudum; the genus as newly validated is Gerocynips, new genus (with G. siberica Kovalev as type species); and the family as validated is Gerocynipidae, new family. The fossil records of Cynipoidea are summarized.