Literature suggests that women experience ovulatory shifts in risk-taking behaviours across different domains, which might be partly attributed to changes in testosterone (T). Thus, we investigated associations between menstrual variability in T concentrations and economic risk-related decisions among athletic women. Thirty-five women were monitored across three consecutive menstrual cycles. Testing occurred on day seven (D7), 14 (D14) and 21 (D21) following the onset of menses. The morning (7 to 8 am) assessment of salivary T (sal-T) and cortisol (sal-C) was followed by the economic Hawk-Dove game (11 am to 12 pm) played in pairs, where hawk decisions were used to index risk. Morning sal-T concentration increased from D7 to D14, before decreasing on D21 (p < 0.001), representing moderate effect size (ES) changes of 0.6 to 0.8. Morning sal-C did not vary over time. Hawk choices paralleled the sal-T results, being elevated on D14 (p < 0.001) with large ES changes of 1.8. Regression analyses revealed that morning sal-T concentration was positively related (p ≤ 0.01) to the number of hawks chosen between- (beta = 0.47) and within-participants (beta = 0.10) when controlling for training hours and menstrual day. In summary, the risk-related choices of athletic women during a dyadic contest covaried with morning sal-T concentrations across the menstrual cycle. Both outcomes were positively correlated on a within- and between-person level. Confirming the major sources of T variation across the menstrual cycle, whilst discerning its relationship with other risk-related behaviours, would be worthwhile avenues for research.