Eight field studies were conducted over a 3-yr period from 2008 to 2010 in Ridgetown, Ontario, Canada, to determine the cumulative stress caused by simulated glyphosate spray drift followed by an in-crop application of metribuzin in processing tomato. As the simulated glyphosate spray drift rate increased so did the degree of injury to the tomatoes. At a simulated spray drift rate of 22.5 g ae ha−1 (2.5% of the recommended glyphosate field rate), a 23% decrease in red tomato yield was observed. Yield reductions increased to 88% of the control when 180 g ae ha−1 glyphosate (20% of the recommended field rate) was applied. Similarly when simulated spray drift rates were followed 3 to 5 d later with an in-crop application of metribuzin at 250 g ai ha−1, tomato yields decreased by 22 to 85% depending on glyphosate rate applied. A transient synergistic interaction was observed only when 22.5 g ae ha−1 glyphosate was followed by metribuzin. The synergistic response was no longer evident by the 28-d injury rating. Herbicide interactions were additive for crop injury, dry weight, fruit counts, and yield when glyphosate spray drift rates of 45, 90, or 180 g ae ha−1 were followed by metribuzin.