Mating order can have important consequences for the fertilization success of males whose ejaculates compete to fertilize a clutch of eggs. Despite an excellent body of literature on mating–order effects in many animals, they have rarely been considered in marine free–spawning invertebrates, where both sexes release gametes into the water column. In this study, we show that in such organisms, mating order can have profound repercussions for male reproductive success. Using in vitro fertilization for two species of sea urchin, we found that the‘fertilization histor’ of a clutch of eggs strongly influenced the size distribution of unfertilized eggs, and consequently the likelihood that they will be fertilized. Males that had first access to a batch of eggs enjoyed elevated fertilization success because they had privileged access to the largest and therefore most readily fertilizable eggs within a clutch. By contrast, when a mal's sperm were exposed to a batch of unfertilized eggs left over from a previous mating event, fertilization rates were reduced, owing to smaller eggs remaining in egg clutches previously exposed to sperm. Because of this size–dependent fertilization, the fertilization history of eggs also strongly influenced the size distribution of offspring, with first–spawning males producing larger, and therefore fitter, offspring. These findings suggest that when there is variation in egg size, mating order will influence not only the quantity but also the quality of offspring sired by competing males.