Testosterone has been theorized to direct status-seeking behaviors, such as competitive decision-making. However, individual differences in basal cortisol and cues that signal an opponent’s status (an opponent’s gender or a prior win/loss in a competition) may moderate testosterone’s relationship with status-seeking behavior. This experiment (n = 115) examines the causal effect of testosterone treatment on men’s competitive behavior before and after receiving relative performance feedback (i.e. win/loss feedback) in mixed-gender math competitions, while also accounting for the moderating role of endogenous basal cortisol. Men given testosterone treatment who had high basal cortisol showed an increased tendency to compete against female opponents and avoid competition against male opponents; men given testosterone treatment who had low basal cortisol showed the opposite pattern (OR = 2.54, 95%CI [1.47, 4.37], p<.001). After providing trial-by-trial feedback, men given testosterone who had high basal cortisol re-entered competitions against low status opponents (prior losers) and avoided competition against high status opponents (prior winners); men given testosterone who had low basal cortisol preferred to re-enter competitions against high status opponents (prior winners) and avoid low status opponents (prior losers; OR = 10.21, [1.84, 56.54], p = .008). These results provide experimental support for a context-dependent dual hormone hypothesis: Testosterone flexibly directs men’s competitive behavior contingent on basal cortisol levels and cues that signal an opponent’s status.