Wheat is one of the main grain species as well as one of the most important crops, being the basic food ingredient of people and livestock. Due to the importance of wheat production scale, it is advisable to predict its yield before harvesting. However, the current models are built solely on the basis of quantitative data. Therefore, the aim of the work was to create three multicriteria models for the prediction and simulation of winter wheat yield, which were made on the basis of extended quantitative and qualitative variables from field research in the year period 2008–2015. Neural networks with MLP (multi-layer perceptron) topology were used to build the following models, which can predict and simulate the yield on three dates: 15 April, 31 May, and 30 June. For this reason, they were designated as follows: QQWW15_4, QQWW31_5, and QQWW30_6. Each model is based on a different number of independent features, which ranges from 19 to 25. As a result of the conducted analyses, a MAPE (mean absolute percentage error) forecast error from 6.63% to 6.92% was achieved. This is equivalent of an error ranging from 0.521 to 0.547 t·ha−1, with an average yield of 6.57 ton per hectare of cultivated area. In addition, the most important quantitative and qualitative factors influencing the yield were also indicated. In the first predictive range (15 April), it is the average air temperature from 1 September to 31 December of the previous year (T9-12_PY). In the second predictive range (31 May) it is the sum of precipitation from 1 May to 31 May, and in the third (30 June) is the average air temperature from 1 January to 15 April of the year (T1-4_CY). In addition, one of the qualitative factors had a significant impact on the yield in the first phase-the type of forecrop in the previous year (TF_PY). The presented neural modeling method is a specific extension of the previously used predicting methods. An element of innovation of the presented concept of yield modeling is the possibility of performing a simulation before harvest, in the current agrotechnical season. The presented models can be used in large-area agriculture, especially in precision agriculture as an important element of decision-making support systems.