Limited information exists on the critical time of weed removal (CTWR) with the currently used soybean cultivars in Ontario. A study consisting of eight field experiments was conducted from 2017 to 2019 in Ontario, Canada, to determine the impact of delayed postemergence (POST) herbicide application on soybean yield based on average weed height at application, days after crop emergence (DAE), accumulated crop heat units (CHU) from the date of planting, and soybean growth stage. The regression model estimated the weed size at herbicide application that led to 1%, 2.5%, and 5% yield loss in soybean was 9, 14, and 20 cm under low weed density (averaging 73 to 134 plants m−2) and 3, 4, and 6 cm under high weed density (143 to 153 plants m−2) conditions, respectively. The estimated DAE at herbicide application time that led to 2.5%, 5%, 10%, and 25% yield loss in soybean was 24, 30, 37, and 53 DAE under low weed density and 8, 10, 14, and 23 DAE under high weed density, respectively. The predicted crop stage at herbicide application that resulted in 2.5%, 5%, 10%, and 25% yield loss in soybean was V4, V5, R2, and R5 under low weed density and VE, VC, V1, and V4 under high weed density, respectively. This study concludes that soybean yield loss is influenced by the weed density (low vs/high) and the time of the first POST herbicide application. When the first POST herbicide application was delayed until soybean was at the V2 stage the monetary loss was Can$20.46 and Can$221.20 ha−1 in low and high weed-density environments, respectively.