Cover cropping is limited by seasonal constraints following corn harvest in the Upper Midwest of the United States. Grass, clover, and brassica cover crops can be interseeded in corn; however, this is problematic because cover crops must tolerate herbicide applications to manage weeds. The objective of this research was to determine the tolerance of broadcast interseeded annual ryegrass, oilseed radish, and crimson clover to PRE and POST residual herbicide applications in corn. From 2016 to 2018 field trials were conducted in Michigan to determine the tolerance of annual ryegrass, oilseed radish, and crimson clover to 13 PRE and 14 POST (applied to V2 corn) herbicides. Cover crops were interseeded into corn at the V3 and V6 stages. Greenhouse experiments to evaluate these species were also conducted from 2016 to 2018; PRE and POST herbicides were applied at 1×, 0.5×, and 0.25× (0.25× was PRE only) of field-application rates. Based on these results, annual ryegrass can be interseeded into V3 or V6 corn following a PRE application of atrazine, clopyralid, saflufenacil, bicyclopyrone, isoxaflutole, or mesotrione, or a POST application of atrazine, bromoxynil, or mesotrione. Oilseed radish can be interseeded into V3 or V6 corn following a PRE application of clopyralid, atrazine, S-metolachlor, bicyclopyrone, or isoxaflutole or at V6 following application of acetochlor, dimethenamid-P, or mesotrione. Oilseed radish can also be interseeded following POST application of atrazine (571 g ai ha−1), bromoxynil, fluthiacet, acetochlor, mesotrione, dicamba + diflufenzopyr, or dimethenamid-P + topramezone. In greenhouse trials, crimson clover was tolerant to rimsulfuron, saflufenacil, and pyroxasulfone applied PRE. Annual ryegrass and oilseed radish can be interseeded into corn at the V3 and V6 stages, but special attention must be given to cover crop species selection and herbicide label restrictions when following herbicide applications in corn.