In this chapter, our purpose is to illustrate the complexity of the outcomes of technological change and the concerns of regulators in the European gambling markets. In 2002, the Finnish Betting and Tipping Company, Veikkaus, estimated, that Finns’ Internet gambling decreased its turnover of betting by 10%. Such leakage is a reason why politicians in different states are considering imposing restrictions of online gambling to other parties of the gambling process, such as Internet service providers, banks, and credit card companies. On the other hand, one possible way to caulk the leakage could be to improve the returns of the players, but this has an adverse effect on the social and political objectives of preventing excessive gambling. The recent Gambelli case further indicates that such restrictions might not be considered proportionate and, thus, are against EU law. The diffusion of the Internet also changes the strategies of the industry stakeholders as the interests of potential market entrants, exclusive license holders, regulators, and legislators are now contradictory with the advent of increased gambling possibilities.