The regulation of games of chance bears significant moral, cultural and historical features throughout the EU Member States. The particularities of gambling activities, and notably the risks they entail and the revenues they generate, have determined Member States to strictly regulate this market sector, and indeed, in some cases, to entrust the provision of such services to state-owned monopolies. The proliferation of distance communication technologies in recent years has enabled the provision of games of chance across physical borders between Member States, whereby operators established and licensed in other Member States have started to challenge national regulations in order to gain market access. The Court of Justice has established that gambling activities are subject to the internal-market constraints, and thus capable of restricting the economic freedoms enshrined in the Treaty. In the lack of harmonisation, the Court has in its case-law acknowledged the sovereign right of Member States to regulate their gambling markets with reference to the moral and cultural aspects of gaming. However, insofar as measures enacted in accordance with the principle of subsidiarity amount to a restriction upon the fundamental economic freedoms, they must be justified by overriding reasons of public interest, and fulfil the proportionality requirements. Overriding reasons commonly referred to by Member States are those of consumer protection against addiction and fraud, and the need to eradicate and prevent criminal activities on the gambling market. These policy aims have largely been accepted by the Court as legitimate public order concerns capable of justifying freedom of movement restrictions, and the proportionality assessment has been (save for in some cases) generally left to the referring national courts, which are consistently provided with a set of vague and insufficient guidelines by the Court of Justice. Considering the relatively large amount of preliminary references currently pending before the Court, national courts are in need of more efficient tools for assessing compatibility between national regulatory measures and EU law. Notwithstanding the wide degree of discretion afforded to the Member States’ governments and authorities in defining their policies and the aims that such measures seek to attain, it is argued that the consistency requirement developed by the Court of Justice as an instrumental measure of suitability needs to be clarified in order to fulfil its function. Moreover, a more intense proportionality inquiry by the Court itself is advocated for, whereby it is feasible to require that Member States bear the burden of proof as to the necessity and suitability of restrictive measures. This would both increase legal certainty, and enable Member States to thoroughly review the genuine aims of their restrictive legislation, and adequately address the realities of cross-border gambling.