Field studies were conducted in 2016 and 2017 in Tallassee, AL, to evaluate the effect of preemergence (PRE) herbicide applications pre- and postcrimp in a cereal rye (Secale cereale) cover crop for control of escape weeds in watermelon (Citrullus lanatus). Treatments were arranged in a randomized complete block design with an augmented factorial treatment arrangement with four replications. The augmented factorial arrangement included three levels of PRE herbicides, two levels of application timing, and a nontreated control. PRE herbicide treatments included ethalfluralin (18 oz/acre), fomesafen (2.5 oz/acre), and halosulfuron (0.56 oz/acre). Application timings were precrimp (herbicide applied before crimping and rolling of the cover crop) and postcrimp (herbicide applied after crimping and rolling of the cover crop). A nontreated cover crop only treatment was also included. There were no interactions among application timing and herbicide. Results indicated application timing influenced total weed coverage but not watermelon yield. Total weed coverage was lowest in precrimp applied treatments at 2, 4, and 6 weeks after treatment (WAT). Comparing individual treatments revealed no significant differences among herbicides with respect to watermelon yield; however, all herbicides increased yield compared with the nontreated.