Among the fields of application of the universe constructed through global communication networks is the one in which some individuals simulate, at a competitive and professional level, the performances that characterize traditional sports by replicating them digitally. There is, however, a lack of legal definitions and regulations of the ecosystem with consequent shortcomings on the tax enforcement front, whose rules adapt each time expressions of contributory capacity emerge. Further problems arise regarding the identification of the most appropriate tax treatment of prizes and winnings from participation in e-sports tournaments, as they are played on digital platforms where traditional sports are reproduced. Such income, in fact, is subject to withholding tax only if paid in the context of events expressly provided for by the legislature and involving technical verifications by the competent administrations, which are currently not regulated. In a broader view and with reference to the unstoppable development of artificial intelligence, especially in sports practiced at a high level, a question then arises that will have to be addressed: whether, in the not too distant future, a tax regulation dedicated to digital sports activities will have to be drawn up and whether, if need be, the classic income categories will have to be reformulated so as to intercept all expressions of wealth production not regulated in the current legal framework.