Cover crop mulches have been successful in reducing weed severity in organic soybeans. This study examined six rye cultivars (SRCs) used as cover crops to determine which were most adapted for use with a roller–crimper in the southeastern U.S. To be an effective mulch, a rye cultivar must produce high biomass and reach reproductive growth stage to facilitate mechanical termination via the roller–crimper prior to soybean planting. Rye cultivars were planted at three locations in North Carolina over the 2009 and 2010 growing seasons. Each rye cultivar was mechanically terminated via a roller–crimper implement. Rye cover crops were terminated on two dates and soybeans were immediately no-till planted into the mulch. In 2009, all rye cultivars produced greater than 9000 kg ha−1 rye biomass dry matter (DM) with the exception of Rymin at Plymouth (2009), but in 2010 only the early flowering cultivars produced in excess of 9000 kg ha−1 DM. There were no detectable soybean yield differences between the SRCs and the weed-free checks, and weed control was excellent across all SRCs at both Plymouth and Salisbury (2009). After an unseasonably cold and wet winter in 2010, the late flowering rye cultivars were not fully controlled by the early termination date due to delayed maturation (less than 65% control at 2 WAP) whereas the early flowering cultivars were fully controlled (100% control at 2 WAP). Rye biomass production was below 9000 kg ha−1 DM for the late flowering and dough development rye cultivars. The early-terminated rye plots had greater weed coverage across all SRCs than those from the late termination date (P < 0.01). However, weeds did not impact soybean yield for either of the termination dates. Soybean yield in 2010 was modeled with rye biomass and soybean population used as covariates, and for both termination dates, soybean yield was proportional to rye biomass production. Early flowering rye cultivars offer producers the widest range of termination opportunities that best coincide with their cash crop planting dates.