Watermelon [Citrullus lanatus (Thunb.) Matsum. & Nakai] growers choose transplanting dates every year considering multiple risk factors. Earlier harvests linked to earlier planting typically find more favorable markets, but earlier planting has higher risk of freeze damage. Research also indicates that risk of fusarium wilt (caused by Fusarium oxysporum f. sp. niveum) is higher during cooler weather, adding to the risk of planting earlier. Thus, growers need to balance market risk (e.g., getting a low price) and production risk (e.g., lower harvest or higher cost due to freezing temperatures or disease) in selecting a planting date. The objective of this analysis is to examine the effect of planting date on the distribution of potential economic returns and evaluate whether late planting could be a favorable risk-management strategy. Probability distributions are estimated for key risk factors based on input from watermelon growers, published price data, historical freeze data, experiment station trials, and expert discussions. The distribution of economic returns is then simulated for three planting windows (early, middle, and late) using simulation software. Results demonstrate planting date risk–return tradeoffs and indicate that late planting is unlikely to be preferable to middle planting, even when risk of fusarium wilt is high.