Cover crop residue retention on the soil surface can suppress weeds and improve organic no-till soybean (Glycine max) yield and profitability compared to a tilled system. Appropriate cereal rye (Secale cereale) fall planting date and termination methods in the spring are critical to achieve these benefits. A plot-scale agronomic experiment was carried out from September 2018 to October 2021 in Kutztown, PA, USA to demonstrate the influence of cereal rye planting date (September or October) and mechanical termination method [no-till (I & J roller-crimper, Dawn ZRX roller, and mow-ted) and tilled (plow-cultivate)] on cover crop regrowth density, weed biomass, soybean yield, and economic returns. In one out of three years, the September rye planting accumulated more cover crop biomass than the October planting, but the regrowth of the rye after roller-crimping was greater with this planting date. Cover crop planting date had no effect on total weed biomass and demonstrated varying effects on soybean grain yield and economic returns. The Dawn ZRX roller outperformed the I & J roller-crimper in effectively terminating cover crops, while the I & J roller-crimper demonstrated more uniform weed suppression and led to greater soybean yields over a span of three years. Organic no-till strategies eliminated the need for tillage and reduced variable costs by 14% over plow-cultivated plots, and generated ~19% greater net revenue across the study period (no-till vs tillage = US $845 vs US $711 ha−1). Terminating cereal rye with roller-crimping technology can be a positive investment in an organic soybean production system.