Bread is an integral part of the diet of the world population. Development of bread enriched with biologically active substances, including antioxidants, could be good nutritional support for human health. Among well-studied antioxidants, we can highlight dihydroquercetin, a flavonoid with outstanding antioxidant properties, such as anti-inflammatory activity, immunostimulatory properties, anti-cancer properties, and others. At the same time, the technology of bread enrichment must consider the possible negative effects of the additive on the technological processes and properties of the final product. The present work was carried out to evaluate the effect of dihydroquercetin on the enzymatic processes occurring during dough maturation and the antioxidant properties of the finished bread. Dihydroquercetin was added in amounts of 0.05 g, 0.07 g, and 0.1 g per 100 g of wheat flour and fermented with commercial baker’s yeast (Saccharomyces cerevisiae). The kinetics of pH and total titratable acidity (TTA) during dough fermentation showed that dihydroquercetin caused slight slowing of enzymatic processes. However, the dosage of dihydroquercetin did not cause statistically significant changes in the yeast concentration, which reached a level of 108 KOU/g after 2 h in all dough samples. Loss of dihydroquercetin during fermentation was established at a level of 20–25%. At the same time, an increase in the total amount of flavonoids in the dough after 2 h of fermentation and an increase in values of antioxidant activity were noted. The antioxidant properties of the bread also increased when it was enriched with dihydroquercetin (about 3.5–4 times) despite the fact that the total quantitative loss of antioxidant in the technological process was considerable (about 40%). A protective effect of the bread matrix on flavonoids during digestion was shown. Dihydroquercetin loss was about 25% regardless of the amount applied. This work clearly showed that addition of dihydroquercetin to a bread formulation represents a promising strategy for increasing the antioxidant properties of bread.