Proprioception is essential for neuromuscular control in relation to sport injury and performance. The effect of landing heights and loads on ankle inversion proprioceptive performance in individuals with or without chronic ankle instability (CAI) may be important but are still unclear. Forty-three participants (21 CAI and 22 non-CAI) volunteered for this study. The Ankle Inversion Discrimination Apparatus for Landing (AIDAL), with one foot landing on a horizontal surface and the test foot landing on an angled surface (10°, 12°, 14°, 16°), was utilized to assess ankle proprioception during landing. All participants performed the task from a landing height of 10 cm and 20 cm with 100% and 110% body weight loading. The four testing conditions were randomized. A repeated measures ANOVA was used for data analysis. The result showed that individuals with CAI performed significantly worse across the four testing conditions (p = 0.018). In addition, an increased landing height (p = 0.010), not loading (p > 0.05), significantly impaired ankle inversion discrimination sensitivity. In conclusion, compared to non-CAI, individuals with CAI showed significantly worse ankle inversion proprioceptive performance during landing. An increased landing height, not loading, resulted in decreased ankle proprioceptive sensitivity. These findings suggest that landing from a higher platform may increase the uncertainty of judging ankle positions in space, which may increase the risk of ankle injury.