Double-cropping soybean (Glycine max L.) after a winter annual crop is common in Kentucky. The preceding winter annual crop may affect double-crop soybean yield in Kentucky. Producers and agronomists have reported greater double-crop soybean yields when preceded by winter canola (Brassica napus L.) rather than winter wheat (Triticum aestivum L.). Explanations for these yield differences remain unresolved. The objectives of this study are to: (1) evaluate double-crop soybean productivity in field environments following four winter annual crop treatments; (2) determine differences of early soybean growth in greenhouse (GH) and cold chamber (CC) environments; and (3) characterize soybean cultivar susceptibility to winter annual leachate in a laboratory. Three winter annuals (canola, barley (Hordeum vulgare L.), wheat) and a non-planted control (fallow) were established in fall 2014 and 2015 near Princeton, KY. Double-crop soybean were established in summer 2015 and 2016. Following winter annual harvest, soil cores were collected for GH and CC experiments. Following winter annual harvest in 2016, stover was collected for laboratory experiments. Results from GH, CC, and laboratory experiments suggest soybean is sensitive to the preceding crop and winter annual leachate. However, yield was not sensitive to the preceding crop