The use of agricultural machines for field operations is often restricted by soil status determined by meteorological conditions several days before the operation. While a projected increase in air temperature caused by climate change may promote evapotranspiration and have positive impacts on the use of agricultural machines, intensified rainfall may have negative effects at the same time. This study aimed to provide probabilistic estimates of climate change impacts the meteorological constraints on field workability of agricultural machines in Hokkaido, Japan. Analyses based on historical meteorological data and machinery operation logs recorded at two agricultural research stations revealed that operations concentrated on days with smaller antecedent precipitation index (API). A simple derivative of API that reflects a practically maximum API value to carry out a certain field operation, termed threshold API, was proposed to evaluate the meteorological constraints on field operations. Because threshold API values for operations that are vulnerable to soil conditions (e.g., sowing and soil preparation) and/or at fields with poor drainage soil were small, this threshold should be a reasonable and quantitative measure of the meteorological constraint on field workability. Using 1-km gridded API values under historical and future climates calculated from a large ensemble dataset of daily mean air temperature and precipitation, we separated workable and unworkable days from June to October based on a threshold value of 5 mm and calculated projected changes in monthly numbers of the total workable day and consecutive unworkable day. While there were slight negative effects in several regions in the Southern and Central regions under future climate with a 4-K higher global mean temperature, preferable changes prevailed in both metrics in the other regions and months. The present results facilitate probabilistic discussion of changes in agricultural calendars and suggest that climate change may extend the agricultural season in Hokkaido.