The APSIM-Wheat and AQUACROP models were calibrated for the Sakha 95 cultivar using phenological data, grain and biomass yield, and genetic parameters based on field observation. Various treatments of planting dates, irrigation, and fertilization were applied over the two successive winter growing seasons of 2019/2020 and 2020/2021. Both models simulated anthesis, maturity dates, grain yield, and aboveground biomass accurately with high performances (coefficient of determination, index of agreement greater than 0.8, and lower values of root mean square deviation) in most cases. The calibrated models were then employed to explore wheat yield and water productivity (WP) in response to irrigation and nitrogen fertilization applications. Scenario analyses indicated that water productivity and yield of wheat ranged from 1.2–2.0 kg m–3 and 6.8–8.7 t ha–1, respectively. Application of 0.8 from actual evapotranspiration and 120% from recommended nitrogen dose was the best-predicted scenario achieving the highest value of crop WP. Investigating the suitable option achieving the current wheat yield by farmers (7.4 t ha–1), models demonstrated that application of 1.4 from actual evapotranspiration with 80% of the recommended nitrogen dose was the best option to achieve this yield. At this point, predicted WP was low and recorded 1.5 kg m–3. Quantifying wheat yield in all districts of the studied area was also predicted using both models. APSIM-Wheat and AQUACROP can be used to drive the best management strategies in terms of N fertilizer and water regime for wheat under Egyptian conditions.