Understanding deracemization is crucial for progress in chiral chemistry, especially for improving separation techniques. Here, we first report the phenomenon of chiral flipping (or reverse deracemization) in a chiral material (i.e., sodium chlorate crystals) during Viedma deracemization, employing a small-volume reactor system for precise analysis. We observe considerable chiral flipping, influenced by the initial imbalance in the numbers of L- and D-form particles. We developed a simple probabilistic model to further elucidate this behavior. We find that the fluctuation in the populations of chiral crystal particles resulting from their random dissolution and regeneration is the key factor behind chiral flipping. This study not only brings to light this intriguing observation of chiral flipping but also contributes to the enhancement of deracemization techniques.