Of all types of Greek benefaction, agonistic festivals – that is, festivals that revolved around athletic, dramatic or cultural contests – may have been the most central to the phenomenon of civic euergetism in the Greek cities of the Hellenistic and Roman period. Core questions of the chapter are: What was the significance of the fact that public festivals were paid and organised by private benefactors? Why did benefactors do this? And what was it that cities stood to gain? The main argument is that agonistic festivals were not simply an object of euergetism but also a medium through which euergetism evolved. They not only were an opportunity for elite benefactors (and athletes) to increase their prestige but were primarily mass events where benefactors and their communities were jointly involved in representing the central social, cultural and political values of the time.