Gambler Queen's Cup is primarily a dating simulation game. The player controls a male protagonist whose goal is to date and eventually have sexual intercourse with three young women he meets at the club. Each date has higher or lower chances of success depending on the amount of money invested in it. Dates are presented as still anime-style images depicting the girl and whatever location the meeting takes place in. A set list of conversation topics is available, as well as a point-and-click interface allowing limited interaction with the environment.