The history of discovery and interpretation of several dinosaurs collected from quarries near the town of Hastings during the latter half of the 19th century is more complicated than it should be. Samuel Husbands Beckles and Charles Dawson collected several large ornithopod skeletons from this area, but just a few bones from these skeletons were subsequently described and interpreted (principally) by Richard Owen and Richard Lydekker. All these specimens merited recognition because they had the potential to contribute to an on-going debate about the anatomical structure and relationships of the iconic Wealden dinosaur Iguanodon. Unfortunately, no detailed description of these important skeletons was published in later years. Furthermore, previously known associations of bones and even provenance information, linked to the specimens that were gradually acquired by the Natural History Museum, are unclear. Confusion may have arisen because Richard Lydekker used the private collector Charles Dawson as a voluntary curatorial assistant. This account documents the past work on the osteology of material that can be attributed to Hypselospinus fittoni. Nearly all such material is described here for the first time, and every effort has been made to re-establish associations between bones as well as provenance information. A skeletal reconstruction of Hypselospinus is attempted on the basis of the hypodigm. Most of the on-going confusion concerning the affinity of this material with either Hy. fittoni or its sympatric contemporary Barilium dawsoni has been resolved. Hypselospinus fittoni (Lydekker, 1889) is rediagnosed on the basis of this new and relatively comprehensive anatomical description, and this animal is compared with known contemporary and closely related taxa. Some recently published accounts claiming to be revisions of the taxonomy of Wealden ‘iguanodonts’, including material belonging to the hypodigm of Hy. fittoni, have failed to adhere to basic taxonomic principles and have caused more confusion than was strictly necessary. The systematic position of Hypselospinus is reassessed cladistically. The cladistic analysis forms the basis for a revised hierarchical classification of derived ornithopods. The consensus topology generated by the systematic analysis has been used to explore the phylogenetic history of these dinosaurs and create an internally consistent classificatory hierarchy (phylogenetic definitions and Linnaean diagnoses are given for critical positions in the topology). This analysis suggests that there is a fundamental split amongst the more derived (clypeodontan) ornithopod ornithischians into the clades Hypsilophodontia and Iguanodontia. There is evidence for anatomical parallelism and convergence (homoplasy) particularly between large-bodied representatives of both clades. Hypselospinus is one of the earliest known styracosternan iguanodontians and displays anatomical characteristics that presage the evolution of the extraordinarily abundant and diverse hadrosaurs of the latest Cretaceous (Campanian−Maastrichtian). These observations cast fresh light on the phylogeny, classification, diversity, and biology of derived ornithopods. There is little doubt that Hy. fittoni could have been understood far better more than a century ago. That this statement is undoubtedly true is reflected in the century of doubt and confusion that has surrounded this taxon and its original incarnation as Iguanodon fittoni.