Annual ryegrass has been proposed as a cover crop in the corn–soybean cropping systems of the U.S. Midwest because of its low seed cost, rapid establishment, contribution to soil quality, weed suppressive abilities, and susceptibility to common broad-spectrum herbicides. However, cover crops can reduce the subsequent main crop yield by creating unfavorable germination and emergence conditions, harboring pests, and if not controlled, competing with the main crop. This study, conducted in Illinois, Oregon, and Tennessee, investigated the efficacy of glyphosate for annual ryegrass winter cover crop removal. Glyphosate at 415, 830, and 1,660 g ae/ha was applied to annual ryegrass at late tiller, second node, boot, and early flowering stages. Annual ryegrass control was consistently maximized with the highest glyphosate rate applied at the boot or early flower stage. Annual ryegrass biomass was generally the lowest with the highest rate of glyphosate applied at the earlier stages. Overall, no single application timing at any glyphosate rate provided complete control or biomass reduction of the annual ryegrass cover crop. A sequential herbicide program or a glyphosate plus a graminicide tank-mix probably will be needed for adequate annual ryegrass stand removal.