Agents seeking an opportunity for profit often have to compete with others who pursue the same opportunity. When having to choose between a number of opportunities differing in their value and if individuals differ in their chances of outperforming others, the choice can be cognitively and emotionally demanding. We explore choice between opportunities using stylized Lions–Foxes games. In such a game, each of three players, with different odds of beating others, has to choose one of two contests that offer different rewards. After game theoretically analyzing the games, which we have experimentally employed, we report four experiments that vary in choice elicitation (repeated play or strategy method), in players' matching (random strangers or partners) and in rewards. Regarding contest choices, we found the choice of the higher value (and seemingly more prestigious) contest to be positively related to winning odds, contrary to what four out of the five (mixed, partially mixed, or pure) equilibria predict. Participants started out rather optimistic, with a large majority choosing the higher value option, but with experience, they approached the only viable of two pure strategy equilibria. Still, mixing continued via reacting to past play and outcome, apparently balancing dissatisfaction from choosing either contest.