Long winters in the Red River Valley (RRV) of eastern North Dakota and western Minnesota result in short growing seasons for corn (Zea mays L.)–soybean (Glycine max L. Merr.) systems. Historically, producers implement aggressive tillage to warm the soil, which has caused hesitation when considering reduced tillage systems. The association between soil warming–drying and crop yields via research at farmer-operated, production-scale systems practicing reduced tillage is lacking. A two-year study was conducted at three producer-operated, corn–soybean fields in the RRV with five soil series ranging from sandy loams to silty clays. Soil temperature (T), soil volumetric water content (θ), and crop yields were measured to evaluate the effects of soil warming and drying and crop performance under reduced tillage practices of vertical tillage (VT), strip tillage with shanks (STS), strip tillage with coulters (STC), and chisel plow (CP). Results showed that daytime soil T and θ in the tilled strips for STC and STS (i.e., in the plant rows) were similar to CP and significantly different from VT. The ST treatments demonstrated added benefits of higher soil θ between the tilled strips (i.e., between the plant rows) during the mid-growing season when plant water needs are at their highest. However, daily averaged soil T and θ demonstrated little to no significant differences among the tillage treatments. Moreover, crop yields were inconsistent with soil T and θ, indicating weak to no practical association in these on-farm settings.