This paper considers a range of visualisations of the face, from the pioneering maxillofacial surgical practice of H.D. Gillies to present-day surgery and art. Gillies’s approach to operation planning and documentation was directly informed by visualisation in the form of his own drawings and the pastels created by Henry Tonks during their collaboration at Aldershot in 1915-17. This ground-breaking partnership is revisited in recent dialogue between maxillofacial surgeons and artists, including that between Thompson and Hartley, Hutchison and Gilbert (Saving Faces), and in the sculptor Luke Shepherd’s training courses for surgeons. Shepherd’s sculptural methods aim to reimmerse the surgeon in a ‘visual language’ (Shepherd 2005), as opposed to the symbolic and linguistic codes by which we conventionally apprehend the face. Such a language, though, is complicated by contemporary maxillofacial techniques, which include growing use of virtual surgical planning and navigational maxillofacial surgery using virtual models. The implications of these contrasting approaches are assessed: in particular the promised creation of ‘secure knowledges’ (Kuppers 2007) by medical imaging is contrasted with the mediated and relative understandings of the face suggested by virtual technologies.