The flour functionality and particle size distribution of wheat flour obtained on roller milling are dependent on the type of wheat, tempering conditions, and milling conditions. In this study, the impact of the tempering conditions (moisture and time) on the chemical and rheological properties of flour from blends of hard red wheat were analyzed. The wheat blends B1-25:75 (hard red spring (HRS)/hard red winter (HRW)), B2-50:50, and B3-75:25, which were tempered to 14%, 16%, and 18% for 16, 20, and 24 h, respectively, were milled using a laboratory-scale roller mill (Buhler MLU-202). Protein, damaged starch, and particle characteristics were influenced by blending, tempering, and milling streams. For all the blends, the protein content varied significantly among the break flour streams; the damaged starch content varied greatly in the reduction streams. The increased damaged starch content of the reduction streams proportionally increased water absorption (WA). Higher proportions of HRS in the blends significantly decreased the pasting temperature of the dough, as measured using Mixolab. Principal component analysis proved that the protein content was the key determinant in particle characteristics, WA, and pasting properties of the flour, especially in blends with a higher proportion of HRS.