Knowledge of weed emergence periodicity can inform the timing and choice of weed management tactics. We tested the effects of weed management system (conventional [CNV] and herbicide-free [HF]), timing of rye sowing (two dates), timing of soybean planting (5 planting dates, 3 in each system), and supplemental control (with and without) on weed suppression and weed community composition in soybean no-till planted into a cereal rye cover crop. Cereal rye was terminated with a roller-crimper and herbicide (CNV) or with a roller-crimper alone (HF), and supplemental weed control was achieved with a postemergence glyphosate application (CNV) or with interrow high-residue cultivation (HF). Supplemental control with glyphosate in CNV was more effective than high-residue cultivation in HF. When soybean was planted on the same date, CNV resulted in less weed biomass and a more even community composition, whereas HF resulted in greater weed biomass, dominated by common ragweed. When we controlled for cereal rye biomass and compared the effects of cereal rye sowing and termination timing within each system, earlier management reduced weed biomass in HF, but tended to increase weed biomass in CNV. Our results suggest the ability to control emerged weeds prior to soybean planting is an important factor that influences the optimal cereal rye cover crop management timing for weed suppression.