Desiccation cracking frequently occurs in mud, clay, and pavement. Understanding the evolution of desiccation cracking may facilitate the development of techniques to mitigate cracking and even prevent it from developing altogether. In this study, experimental investigations were performed focusing on the effects of fibers on the evolution of desiccation cracking in soil-cement. Varied types of fibers (i.e., jute fiber and polyvinyl alcohol fiber (PVA)) and fiber contents (i.e., 0%, 0.25%, 0.5%, and 1%) were involved. The digital image correlation (DIC) method was employed to capture the evolution and propagation of cracks in the soil-cement specimens when subjected to desiccation. The results show that the presence of fibers imposes significant effects on the crack propagation pattern as well as the area and length of the cracks in the soil-cement during shrinkage. The addition of fibers, however, insignificantly affects the evaporation rate of the specimens. The crack area and crack length of the specimens decreased significantly when more fibers were included. There were no macroscopic cracks observed in the specimens where the fiber content was 1%. The DIC method effectively helped to determine the evolution of displacement and strain field on the specimens' surface during the drying process. The DIC method is therefore useful for crack monitoring.