The historic maternal environment; the identity of competing, neighboring plants; and biotic stresses, such as fungal disease and herbivory, interact to influence the competitive ability, reproductive output, and plasticity of weed populations. A weed capable of altering its phenotype in response to environmental factors is better able to compete for resources in agroecosystems, thereby reducing crop yields and contributing more seeds to the seed bank. Velvetleaf is a highly competitive annual weed in many North American cropping systems, exhibiting a high degree of phenotypic plasticity in response to biotic and abiotic factors. We examined the effects of seed size (small and large), competitive environment (with and without soybean), and stress level (none = no treatment, moderate = pathogen inoculation, high = pathogen plus herbicide) on velvetleaf allometry and reproductive output during three field seasons. Only under the high-stress treatment was velvetleaf biomass, height, and reproductive output compromised (> 15% each), and these traits were further reduced with soybean competition. Soybean competition alone reduced velvetleaf biomass (> 50%), height (25%), and seed output (50%), but effects of competition varied with stress level. Velvetleaf plants that originated from large seeds (≥ 10 mg) generally outperformed plants originating from small seeds (< 10 mg) except under the high-stress treatment. These findings suggest that velvetleaf life-history traits and reproductive output in the current generation are a function of both present and historic factors. Management strategies for this species should involve tactics that not only reduce its competitive ability (e.g., biomass, height) but also decrease its seed production via synergistic stressors such as increased crop competitiveness, reduced-rate herbicide applications, and pathogen infection.