The high intra-seasonal rainfall variability and the lack of adaptive capacities are the major limiting factors for rainfed agricultural production in smallholder farming systems across Sub-Saharan Africa. Therefore, the crop planting date, a low-cost agricultural management strategy aiming to alleviate crop water stress can contribute to enhance agricultural decision-making, particularly as a climate change adaptation strategy. By considering the crop water requirements throughout the crop growing cycle using a process-based crop model in conjunction with a fuzzy rule-based planting date approach, location-specific planting rules were derived for maize cropping in Burkina Faso (BF). Then, they were applied to regional future climate projections to derive optimized planting dates (OPDs) for the 2020s (2011–2030) and the 2040s (2031–2050), respectively. Based on potential maize yield simulations driven by climate change projections and planting dates, the OPD approach was compared with a well-established planting date method for West Africa and evaluated as a potential adaptation strategy for climate change. On average, the OPD approach achieved approximately +15% higher potential maize yield regardless of the regional climate model (RCM) and the period. However, the potential yield surpluses strongly decreased from the North to the South. Regarding climate change adaptation, the combined impact of climate change and the OPD approach has shown on average, a mean maize yield deviation between −23% and 34% in comparison to the 1989–2008 baseline period. Yield deviation is found to depend strongly on the RCM and location. The RCM ensemble mean yield for the period 2011–2050 revealed a maximum decrease of 8% compared to the baseline period. On the one hand, these findings highlight the potential of the OPDs as a crop management strategy but, on the other hand, it is apparent that farmers need to combine the OPDs with others suited farming practices to adequately respond to climate change.