The number of ovules per flower varies over several orders of magnitude among angiosperms. Here we consider evidence that stochastic uncertainty in pollen receipt and ovule fertilization has been a selective factor in the evolution of ovule number per flower. We hypothesize that stochastic variation in floral mating success creates an advantage to producing many ovules per flower because a plant will often gain more fitness from occasional abundant seed production in randomly successful flowers than it loses in resource commitment to less successful flowers. Greater statistical dispersion in pollination and fertilization among flowers increases the frequency of windfall success, which should increase the strength of selection for greater ovule number per flower. We therefore looked for evidence of a positive relationship between ovule number per flower and the statistical dispersion of pollen receipt or seed number per flower in a comparative analysis involving 187 angiosperm species. We found strong evidence of such a relationship. Our results support the hypothesis that unpredictable variation in mating success at the floral level has been a factor in the evolution of ovule packaging in angiosperms.