Recent findings in behavioral economics have shown that an individual may not always act optimally and rationally in their decision-making. However, these findings have come mainly from laboratory conditions, and as such, they need to be verified under real circumstances. This paper examines the presence of heuristics in the environment of fantasy sports. The data come from a fantasy league based on the National Hockey League in the season of 2015–16. Its users come mainly from the Czech Republic. The results show a moderately strong presence of representativeness. Nevertheless, there are also manifestations of not always prioritizing point-maximizing strategies, for example in the higher demand for hockey players of the same nationality as that of the users. However, the main factor influencing the demand is still the athletes’ performance. This study’s findings hold implications for fantasy sports, prompting fantasy sports participants to strategically adjust squad selection. For platforms, it suggests user experience enhancements and algorithmic adjustments to guide optimal decision-making, enriching overall engagement. Additionally, the research contributes to decision-making theory by validating behavioral economics in the real world, emphasizing context-specific biases, and advocating for an integrated understanding of heuristics and rational factors in decision environments.