Attending school is a multifaceted experience. Students are not only exposed to new knowledge but are also immersed in a structured environment in which they need to respond flexibly in accordance with changing task goals, keep relevant information in mind, and constantly tackle novel problems. To quantify the cumulative effect of this experience, we examined retrospectively and prospectively, the relationships between educational attainment and both cognitive performance and learning. We analyzed data from 196,388 subscribers to an online cognitive training program. These subscribers, ages 15-60, had completed eight behavioral assessments of executive functioning and reasoning at least once. Controlling for multiple demographic and engagement variables, we found that higher levels of education predicted better performance across the full age range, and modulated performance in some cognitive domains more than others (e.g., reasoning vs. processing speed). Differences were moderate for Bachelor's degree vs. High School (d = 0.51), and large between Ph.D. vs. Some High School (d = 0.80). Further, the ages of peak cognitive performance for each educational category closely followed the typical range of ages at graduation. This result is consistent with a cumulative effect of recent educational experiences, as well as a decrement in performance as completion of schooling becomes more distant. To begin to characterize the directionality of the relationship between educational attainment and cognitive performance, we conducted a prospective longitudinal analysis. For a subset of 69,202 subscribers who had completed 100 days of cognitive training, we tested whether the degree of novel learning was associated with their level of education. Higher educational attainment predicted bigger gains, but the differences were small (d = 0.04-0.37). Altogether, these results point to the long-lasting trace of an effect of prior cognitive challenges but suggest that new learning opportunities can reduce performance gaps related to one's educational history.