The wheat/double crop soybean system has been investigated thoroughly in the Southeast region, however less emphasis has been placed on investigating other winter crop scenarios, such as emerging specialty winter grain crops. In addition, cover crop adoption is increasing rapidly in North Carolina, justifying research efforts to understand cover crop impact on soybean production and to ultimately advise soybean producers on cover crop management that will help maximize soybean production. In 2019, a trial was installed at two research locations, Rocky Mount and Salisbury, to investigate the impact of various winter crop scenarios and soybean maturity groups on soybean yield. Three soybean maturity groups (III, V, VII) were evaluated across six winter crop scenarios including: May fallow planting, planting behind acereal rye cover crop, planting behind a cereal rye/crimson clover cover crop, June fallow planting, planting behind a wheat grain crop, and planting behind a rapeseed grain crop. Preliminary results indicate that winter crop biomass will be highest with cereal rye in an environment with adequate N fertility, however in an environment with low residual N, biomass production from an unfertilized cereal rye and fertilized wheat crop could be comparable. Soybean stand was reduced following winter crop scenarios with high levels of biomass production (>6000 lbs/A). In general, soybean yields were highest with the maturity group V and VII varieties, and lower with the maturity group III variety. Winter crop impact on soybean yield varied by site.