This study aimed to compare time-to-boundary and sample entropy during a single-leg balance task between individuals with chronic ankle instability (CAI), lateral ankle sprain copers, and healthy controls. Twenty-two participants with CAI, 20 lateral ankle sprain copers, and 24 healthy controls performed a single-leg balance task during an eyes-closed condition. Participants with CAI exhibited lower time-to-boundary values compared with lateral ankle sprain copers and healthy controls. However, we did not find differences in sample entropy variables between cohorts. A decrease in time-to-boundary values in participants with CAI indicated that CAI may constrain the ability of the sensorimotor system to maintain the center of pressure within the boundaries of the base of support. However, the regularity of the center of pressure velocity time series appears not to be altered in the CAI cohort in this study.