The incorporation of cover crops into the maize (Zea mays L.)-soybean [Glycine max (L.) Merr.] rotation in the U.S. upper Midwest may improve sustainability. Long, cold winters in the region make identifying successful cover crop species and management practices a challenge. Two experiments were conducted in Minnesota, USA from fall 2016 through spring 2019 to examine the effect of cover crops interseeded at four- to six-leaf collar (early-interseeded) and dent to physiological maturity (late-interseeded) on biomass and grain yield of maize. Annual ryegrass (Lolium multiflorum L.) and cereal rye (Secale cereale L.) were evaluated as monocultures and in mixtures with crimson clover (Trifolium incarnatum L.) and forage radish (Raphanus sativus L.). Differences in canopy cover and biomass of late-interseeded cover crops were observed at the southernmost location in 2018. Additional accumulated growing-degree days in fall 2018 did not translate into increased cover crop canopy coverage of late-interseeded cover crops. Differences in cover crop canopy cover and biomass of early-interseeded cover crops were observed by fall frost at all locations in 2017 and at the northernmost location in 2018. Cover crop canopy cover and biomass at termination before planting maize, soil moisture at maize planting as well as maize aboveground biomass and yield were not affected by spring cereal rye regrowth of cover crops late-interseeded the previous year. Similarly, early-interseeded cover crops did not affect maize aboveground biomass or yield. We attribute these results to limited cover crop growth. This highlights the potential of a variety of cover crop strategies interseeded into maize in the U.S. upper Midwest; however, efforts to fine-tuning cover crop management and weather conditions are needed to benefit from such practice.