<p>Sub-Sahara African agriculture is susceptible to variable precipitation pattern due to its reliance on rainfed agriculture. A study was carried out in Burkina Faso and Senegal, West Africa to (i) characterize the climate and assess the occurrence of meteorological drought (hereafter drought) (ii) evaluate the rain onset, cessation, and length of growing period and (iii) identify the optimal planting time for maize, sorghum, pearl millet, and peanut. The daily precipitation data (1981–2020) was obtained from the Climate Hazard Group Infrared Precipitation with Stations (CHIRPS). Weekly cumulative precipitation and evapotranspiration probabilities, along with a crop simulation model, were used to evaluate the rain onset and cessation date, growing season length, and yield. The Z-score method was used to identify the drought years. The results showed that there is a latitudinal difference in precipitation distribution from south to north. Over the past 40 years (1981–2020), at least 14–15% and 12–15% of the years were identified as severe and mild drought years, respectively. The most severe drought occurred between 1981 and 1987 that slightly vary by location. Planting based on weekly precipitation meeting 50% of evapotranspiration in 70% of the long-term seasons (P3) increased major crops yield. Sorghum performs best with early planting (P1) due to its drought tolerance. The northern most locations are dry and the length of growing period is too short. Thus, in the north, climate adaptation policy strategy should focus on use of early planting, drought resistant and quick-maturing crops, along with supplementary irrigation.</p>