The timing and methods of sowing wheat can significantly impact its productivity, especially in the face of climate change. To investigate this, two field experiments were conducted over consecutive winter seasons in 2021/22 and 2022/23 in Kharga Oasis, Egypt. The aim was to assess the effects of five different sowing dates (30^th October, 10^th, 20^th, and 30^th of November, and 10^th of December) using four distinct sowing methods (flatbed broadcast, ridges, rows, and raised-bed) on the productivity of the wheat cultivar Giza 171. The Decision Support System for Agrotechnology Transfer (DSSAT) software was employed to simulate wheat yield. The results of the experiments revealed that planting wheat on the optimal date of 20^th November proved superior for grain yield in the first season. However, the highest grain yield in the second season was achieved with a sowing date of 10^th November, which showed no significant difference compared to the 30^th of October and 20^th of November. Among the different sowing methods, raised-bed cultivation consistently produced the highest values for most of the parameters studied in both growing seasons. Furthermore, the DSSAT model effectively simulated grain yield, total biomass, and harvest index, with the Nash-Sutcliff efficiency (NSE) values exceeding 0.75. The findings highlight the significant impact of sowing dates and patterns on wheat yield and its associated attributes. Moreover, the successful simulation of these effects by the DSSAT model further validates its usefulness in predicting the outcomes of different management practices.