Young-of-year flatfish grow through a series of critical periods in which they are vulnerable to different predators, including decapod crustaceans. The purpose of this study was to determine if winter flounder, Pseudopleuronectes americanus, were vulnerable to one such decapod, the green crab, Carcinus maenas, and to determine if vulnerability differed between wild and cultured fish. To examine the predator–prey size relationship, an experiment was conducted in which six cultured and three wild winter flounder size class treatments were tested against six crab size class treatments. Flounder of all size classes were preyed on by all size classes of green crabs; however, mortality was highest when the largest crabs were matched with the smallest flounder. The number of flounder killed per day was significantly higher (31%) in winter flounder <20 mm compared to all other larger fish size classes (4–8%). Additionally, these fish were attacked at a faster rate than any other fish size class. For the 31–60 mm fish size classes tested, more wild fish (11%) were killed per day by crabs than cultured fish (6.3%). These results suggest that in a winter flounder stock enhancement program, only fish >20 mm should be released to promote post-release survival.