Efficient learning methods are important for cognitive rehabilitation. Studies have compared the learning benefits of errorless and trial-and-error (T&E) methods, focusing primarily on memory functions. Executive function related to error management has also been implicated in the underlying cognitive processes needed for the T&E method, although few studies addressed this issue. Herein, to further investigate learning adaptation involving executive function, we developed an experimental execution task focusing on the error correction process (i.e., the chip task), which required self-error corrections based on error feedback to achieve correct answers. We analyzed the relationships among cognitive performance, age, and T&E learning outcomes in this execution task in older individuals. Fifty older participants performed seven execution task sessions, during which they changed the arrangement of four chips based on error feedback until they were correctly arranged. The learning outcome was defined as the average number of chip replacements required to achieve correct answers in the last two sessions. The T&E learning outcomes were significantly related to cognitive performance but not to age. Our findings demonstrate that T&E learning adaptation in the execution task was influenced by cognitive performance rather than age in older individuals. This suggests that older individuals can learn how to manage errors through the self-error correction process, depending on their residual cognitive functions. The extent to which T&E-based learning methods are incorporated should be tailored to the individual's cognitive ability to utilize residual cognitive functions.