Soybean planting has occurred earlier in the Midwestern United States in recent years; however, earlier planting subjects the crop to longer durations of weed interference. This may change the optimum timing of POST glyphosate applications, or increase the need for residual herbicides applied PRE to optimize yield. A field study was conducted in 2012 and 2013 near Arlington, WI to determine the effect of planting date, residual herbicide use, and POST glyphosate timing on weed control and soybean yield. Planting dates were late April, mid-May, and early June. A PRE application of sulfentrazone plus cloransulam was applied to half the plots following each planting date. Glyphosate was applied POST to all plots at the V1, V2, V4, or R1 soybean growth stage. Planting date and glyphosate timing did not affect soybean yield in this study. However, averaged across years, planting dates, and POST glyphosate timings, yield increased from 3,280 to 3,500 kg ha−1 when a PRE herbicide with residual soil activity was used. In POST-only treatments, delaying the planting date to June decreased weed density at POST application timing from 127 to 5 plants m−2 (96%) and from 205 to 42 plants m−2 (80%) in 2012 and 2013, respectively. Where a PRE was used, total weed density at POST application timing was always less within planting date, and also declined from early to late planting date 26 to 3 plants m−2 (89%) and 23 to 6 plants m−2 (74%) in 2012 and 2013, respectively. In conclusion, both PRE herbicide use and delayed soybean planting were effective strategies to reduce the number of in-crop weeds exposed to POST glyphosate and should be considered as strategies to reduce the number of weeds exposed to POST herbicides for resistance management.