Weeds can cause significant yield loss in watermelon production systems. Commercially acceptable weed control is difficult to achieve, even with heavy reliance on herbicides. A study was conducted to evaluate a spring-seeded cereal rye cover crop with different herbicide application timings for weed management between row middles in watermelon production systems. Common lambsquarters and pigweed species (namely, Palmer amaranth and smooth pigweed) densities and biomasses were often lower with cereal rye compared with no cereal rye, regardless of herbicide treatment. The presence of cereal rye did not negatively influence the number of marketable watermelon fruit, but average marketable fruit weight in cereal rye versus no cereal rye treatments varied by location. These results demonstrate that a spring-seeded cereal rye cover crop can help reduce weed density and weed biomass, and potentially enhance overall weed control. Cereal rye alone did not provide full-season weed control, so additional research is needed to determine the best methods to integrate spring cover cropping with other weed management tactics in watermelon for effective, full-season control.